Downstream synthetic route of 103260-44-2

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

c) To a solution of 425 mg (2.5 mmol) of ethyl 2-(tetrahydro-2H-pyran-4- yl)acetate in 10 mL of dry THF cooled at 05C under argon, a 2.71 mL of a solution of LiAII-U 1 M in THF was added. Bubbling was observed. It was stirred at room temperature for 30 min. Then it was quenched with wet EtAcO, dried with MgS04 and filtered through celite, washing with abundant EtAcO. After removing the solvent the desired compound, 2-(tetrahydro-2H-pyran-4-yl)ethanol, was obtained (300 mg, 93%).

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; DRACONIS PHARMA, S.L.; ALMIRALL, S.A.; TORRENS JOVER, Andoni; MERCE VIDAL, Ramon; CALDENTEY FRONTERA, Francesc Xavier; RODRIGUEZ GARRIDO, Antonio, David; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/37960; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Brief introduction of 103260-44-2

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of lithium diisopropylamide (1.8 M in THF/heptane/ethylbenzne, 3.6 mL, 6.4 mmol) in 10 mL of THF at -78 0C was added trimethylsilyl chloride (1.4 mL, 11 mmol) dropwise via syringe pump. The product of Example 143B (1.0 g, 5.8 mmol) in 5 mL of THF was then added to the mixture dropwise via syringe pump. The mixture was stirred at -78 0C for 2 hours then N-bromosuccinimide (NuBS, 1.1 g, 6.0 mmol) in 10 mL of THF was added dropwise via syringe pump. The reaction mixture was allowed to warm slowly to ambient temperature and was stirred for 16 h. The mixture was then concentrated under reduced pressure and the residue was dissolved in 20 mL of EtOAc, washed 1 X 5 mL of H2O. The aqueous layer was extracted 3 X 5 mL of EtOAc and the combined organic extracts were dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and purified via column chromatography (SiO2, 70% hexanes in EtOAc) to provide the title compound (0.70 g, 2.8 mmol, 48% yield). MS (DCIZNH3) m/z 268 (M+NH4)+., 103260-44-2

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; ABBOTT LABORATORIES; WO2006/69196; (2006); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 103260-44-2

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

c) To a solution of 425 mg (2.5 mmol) of ethyl 2-(tetrahydro-2H-pyran-4- yl)acetate in 10 mL of dry THF cooled at 05C under argon, a 2.71 mL of a solution of LiAII-U 1 M in THF was added. Bubbling was observed. It was stirred at room temperature for 30 min. Then it was quenched with wet EtAcO, dried with MgS04 and filtered through celite, washing with abundant EtAcO. After removing the solvent the desired compound, 2-(tetrahydro-2H-pyran-4-yl)ethanol, was obtained (300 mg, 93%).

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; DRACONIS PHARMA, S.L.; ALMIRALL, S.A.; TORRENS JOVER, Andoni; MERCE VIDAL, Ramon; CALDENTEY FRONTERA, Francesc Xavier; RODRIGUEZ GARRIDO, Antonio, David; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/37960; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 103260-44-2

103260-44-2, As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate(20 g, 116 mmol) in anhydrous THF (300 mE) was addedlithium aluminum hydride (8.8 g, 232 mmol) portionwise at0 C. The mixture was stirred at 11-13 C. for 18 h. TEC(petroleum ether: ethyl acetate=3: 1) showed no startingmaterial remaining. The mixture was quenched with water(9 mE), 10% aq. NaOH solution (9 mE) and water (18 mE)successively at 0 C., filtered and concentrated underreduced pressure to give crude 2-(tetrahydro-2H-pyran-4-yl)ethanol (11.7 g, 77%) as an oil, which was used for thenext step directly without further purification. ?H NMR(CDC13, 400 MHz): oe 3.86-3.90 (m, 2H), 3.58-3.61 (t, J=6.4Hz, 2H), 3.32-3.35 (t, J=11.6 Hz, 2H), 2.69-2.70 (m, 1H),1.61-1.63 (m, 3H), 1.54-1.60 (m, 2H), 1.43-1.45 (m, 2H).

103260-44-2, As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; Vitae Pharmaceuticals, Inc.; Claremon, David A.; Yuan, Jing; Zhao, Wei; Zheng, Yajun; (54 pag.)US9481674; (2016); B1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Some tips on 103260-44-2

The synthetic route of 103260-44-2 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

To a solution of (Tetrahydro-pyran-4-yl)-acetic acid ethyl ester (2.0 g, 11.6 mmol) in 50 mL of THF at -78 C. LDA (1.0 M, 17.4 mL, 34.8 mmol) is added dropwise. The solution is stirred for 0.5 h and treated with HMPA (3.2 mL, 9.3 mmol) and MeI (4.94 g, 34.8 mmol). The reaction mixture is stirred at the same temperature for 0.5 h and for 1.5 h at 0 C., acidified with aqueous 1 N aqueous HCl solution, and extracted twice with ether (2¡Á40 mL). The organic phase is washed with saturated aqueous NaCl solution, dried (MgSO4), and concentrated in vacuo to give 1.8 g of 2-(Tetrahydro-pyran-4-yl)-propionic acid ethyl ester which is hydrolyzed without further purification., 103260-44-2

The synthetic route of 103260-44-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Breitenstein, Werner; Erhardt, Claus; Maibaum, Juergen Klaus; Ostermann, Nils; Zimmermann, Juerg; Masuya, Keiichi; Konishi, Kazuhide; Yokokawa, Fumiaki; Kanazawa, Takanori; Jacoby, Edgar; Marzinzik, Andreas; Grosche, Philipp; Kawakami, Shimpei; US2009/233920; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

New learning discoveries about 103260-44-2

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

Preparatory Example 33 4-Tetrahydropyranylacetic acid STR234 20 ml of methanol, 10 ml of water and 1 g of sodium hydroxide were added to 0.9 g of ethyl 4-tetrahydropyranylacetate and agitated at 80¡ã C. for 1 hour. The solvent was removed by distillation, to which water was added. After washing with ethyl acetate, a hydrochloric acid aqueous solution was added to the resultant aqueous phase to an extent of pH of 3, followed by extraction with chloroform under salting-out conditions and drying with anhydrous magnesium sulfate. This was removed by filtration and the solvent was distilled off, thereby obtaining 0.87 g of a crude intended compound. 1 H-NMR(CDCl3) delta:1.0-2.4(m,5H), 2.28(bd,J=6.5 Hz,2H), 3.37(td,J=11.5 Hz,2.9 Hz,2H), 3.7-4.1(m,2H), 7.85(bs,1H), 103260-44-2

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; Eisai Co., Ltd.; US5221671; (1993); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 103260-44-2

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of sodium hydroxide (15.9 g, 44.06 mmol) in water (150 ml) was added dropwise to a solution of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (15 g, 8.81 mmol) in methanol (150 ml) at a temperature of 0 ¡ãC or below, and the mixture was stirred at room temperature for 15 hr. The solvent of the reaction mixture was removed by distillation under reduced pressure, and the water layer was adjusted to pH 3 by the addition of 1 M hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure to give a corresponding acid as a colorless solid (12.0 g, 94percent). This compound was used in the next step without further purification. Benzyl bromide (14.3 g, 83.33 mmol) was added dropwise to a suspension of this compound (10.0 g, 69.44 mmol) and anhydrous potassium carbonate (28.8 g, 208.3 mmol) in acetonitrile (100 ml) at room temperature, and the mixture was refluxed for 48 hr. The solvent of the mixture was removed by distillation under reduced pressure, the residue was diluted with water and was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate = 9:1) to give the tile compound as an oil (12.0 g, yield 75percent). 1H-NMR (400 MHz, CDCl3): delta (ppm) 7.39-7.34 (m, 5H), 5.12 (s, 2H), 3.95-3.92 (m, 2H), 3.42-3.36 (m, 2H), 2.30 (d, J = 7.2 Hz, 2H), 2.09-1.99 (m, 1H) 1.64-1.61 (m, 2H), 1.39-1.29 (m, 2H); MS (ESI): m/z 234 (M+).

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Meiji Seika Pharma Co., Ltd.; MORINAKA, Akihiro; MAEBASHI, Kazunori; IDA, Takashi; HIKIDA, Muneo; YAMADA, Mototsugu; ABE, Takao; EP2737900; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Simple exploration of 103260-44-2

103260-44-2, The synthetic route of 103260-44-2 has been constantly updated, and we look forward to future research findings.

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

80 mg (0.38 mmol) of Example 11 B were dissolved in 1 ml_ of absolute ethanol, 262 mg (1.52 mmol) of ethyl tetrahydropyran-4-yl-acetate, and 45.1 mg (1.10 mmol) of sodium hydride (60 % suspension in mineral oil) were added. The reaction mixture was heated to 1500C for 40 min in a microwave oven. Cooling to 200C was followed by evaporation of the solvent under reduced pressure. The residue was treated with water (10 ml_), acidified with HCI (10 % in water) and extracted two times with dichloromethane (2 ml_). The organic layer was dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure. The residue was triturated with ether to give 65 mg (53.7 %) of the product as a white solid.HPLC-MS (Method Grad_C8_NH4COOH): Rt: 1.89 minMS (ESI pos): m/z = 319 (M+H)+.

103260-44-2, The synthetic route of 103260-44-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/121919; (2009); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Analyzing the synthesis route of 103260-44-2

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.103260-44-2,Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate,as a common compound, the synthetic route is as follows.

A solution of sodium hydroxide (15.9 g, 44.06 mmol) in water (150 ml) was added dropwise to a solution of ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate (15 g, 8.81 mmol) in methanol (150 ml) at a temperature of 0 C or below, and the mixture was stirred at room temperature for 15 hr. The solvent of the reaction mixture was removed by distillation under reduced pressure, and the water layer was adjusted to pH 3 by the addition of 1 M hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure to give a corresponding acid as a colorless solid (12.0 g, 94%). This compound was used in the next step without further purification. Benzyl bromide (14.3 g, 83.33 mmol) was added dropwise to a suspension of this compound (10.0 g, 69.44 mmol) and anhydrous potassium carbonate (28.8 g, 208.3 mmol) in acetonitrile (100 ml) at room temperature, and the mixture was refluxed for 48 hr. The solvent of the mixture was removed by distillation under reduced pressure, the residue was diluted with water and was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on silica gel column (hexane:ethyl acetate = 9:1) to give the tile compound as an oil (12.0 g, yield 75%). 1H-NMR (400 MHz, CDCl3): delta (ppm) 7.39-7.34 (m, 5H), 5.12 (s, 2H), 3.95-3.92 (m, 2H), 3.42-3.36 (m, 2H), 2.30 (d, J = 7.2 Hz, 2H), 2.09-1.99 (m, 1H) 1.64-1.61 (m, 2H), 1.39-1.29 (m, 2H); MS (ESI): m/z 234 (M+)., 103260-44-2

As the paragraph descriping shows that 103260-44-2 is playing an increasingly important role.

Reference£º
Patent; Meiji Seika Pharma Co., Ltd.; MORINAKA, Akihiro; MAEBASHI, Kazunori; IDA, Takashi; HIKIDA, Muneo; YAMADA, Mototsugu; ABE, Takao; EP2737900; (2014); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

Downstream synthetic route of 103260-44-2

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various.

103260-44-2, Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate 32: 2-(Tetrahydro-2/-/-pyran-4-yl)ethanolTo an ice-cold solution of lithium aluminium hydride (12.6 ml, 2.3M solution in tetrahydrofuran) in dry tetrahydrofuran (20 ml) and under nitrogen, was added a solution of ethyl tetrahydro-2/-/-pyran-4-yl acetate (5g) in dry tetrahydrofuran dropwise over 10 minutes. Following the addition the reaction was heated to reflux, overnight. The reaction was cooled and diluted with diethyl ether (100 ml). A 5M aqueous solution of sodium hydroxide (-10 ml) was added cautiously to the reaction mixture until the effervescence ceased. The formed white precipitate was filtered off. The resulting filtrate was dried over potassium carbonate, filtered and concentrated in vacuo. This yielded the title compound as a colourless oil (3.3g). MS calcd for (C7H14O2)” = 130 MS found (electrospray): (M+H)+ = 1311 H NMR (DMSO): 4.35 (1 H, t), 3.80 (2H, m), 3.43 (2H, m), 3.25 (2H, m), 1.60 (1 H, m), 1.54 (2H, m), 1.35 (2H, m), 1.13 (2H, m).

103260-44-2, 103260-44-2 Ethyl 2-(tetrahydro-2H-pyran-4-yl)acetate 2773412, aTetrahydropyrans compound, is more and more widely used in various.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/101867; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics