Category: 1768-64-5

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

Example 1 Preparation of 1-(4-tetrahydropyranyl)but-1-en-3-one 5.0 g of magnesium were introduced into 100 ml of anhydrous tetrahydrofuran. 25 g of 4-chlorotetrahydropyran were added dropwise under reflux under a nitrogen atmosphere, and the mixture was refluxed for 2 hours. A solution of 23.5 g of 1-(dimethylamino)but-1-en-3-one in 20 ml of anhydrous tetrahydrofuran was subsequently added dropwise to the reaction mixture, cooled to from 0 to 5 C., at a rate such that the internal temperature did not exceed 50 C., and the mixture was stirred at room temperature for a further 2 hours. For work-up, the reaction mixture was poured into a mixture of ice and dilute HCl, and extracted 3 times with 200 ml of chloroform, and the extracts were washed with saturated sodium chloride solution and dried over MgSO4. Removal of the solvent gave 24.0 g (75%) of 1-(4-tetrahydropyranyl)but-1-en-3-one having a boiling point of 117 C./10 mmHg.

1768-64-5, The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BASF Aktiengesellschaft; US5221753; (1993); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixrue of 4-chlorotetrahydro-2H-pyran (1 g, 8.29 mmol) and potassium ethanethioate (0.947 g, 8.29 mmol) in DMF (15 mL) was stirred at 80 C. for 24 h. The reaction mixture was cooled down and partitioned between hexane and cold 1N Na OH. The organic layer was washed with brine, dried (MgSO4), removed the solvent to afford S-tetrahydro-2H-pyran-4-yl ethanethioate as a pale brown oil. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 1.68 (2 H, m), 1.90 (2 H, m), 2.32 (3 H, s), 3.55 (2 H, m), 3.68 (1 H, m), 3.91 (2 H, dt, J=11.83, 3.90 Hz).

1768-64-5, 1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; US2008/226592; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2.0 mmol of the compound 5-hydroxy-2,3-dihydro-[1,4]dioxane[2,3-f]quinazolin-10(7H)-one represented by the formula (8) was dissolved in 15 ml of DMF. Add potassium carbonate (550 mg, 4.0 mmol) at room temperature for half an hour, slowly add 3.0 mmol of 4-chlorotetrahydro-2H-pyran to the system, heat to 80 C, react for 6-8 h, and check the progress of the reaction by TLC. After the completion of the reaction, the mixture was poured into 30 ml of ice water and suction filtered to give 5-((tetrahydro-2H-pyran-4-yl)oxy)-2,3-dihydro-[1,4]dioxane [2,3-f]quinazolin-10(7H)-one, yield: 75%., 1768-64-5

1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; Beijing University of Technology; Hu Liming; Fan Haoru; Wei Dengshuai; Zeng Chengchu; (19 pag.)CN109776551; (2019); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

To a vigorously stirred suspension of Mg (1.76 g, 72.8 mmol) turnings and iodine (46.1 mg, 0.182 mmol) in THF (2 mL) under N2 was added 1,2-dibromoethane (68.3 mg, 0.364 mmol) and 10% of a solution of 4-chlorotetrahydro-2H-pyran (4.4 g, 36.4 mmol) in THF (18 mL). Themixture was heated to 60C and as the reaction mixture turned clear and Grignard initiatedtook place, the remainder of the solution of 4-chlorotetrahydro-2H-pyran in THF was added slowly over 30 mm. The reaction mixture was stirred at 65C for 2h to give a solution of (tetrahydro2H-pyran-4-yl)magnesium chloride in THF (-2M). The Grignard solution was used without any further purification. The solution of 36-4 (800 mg, 2.06 mmol) in THF (150 mL) under N2 wasadded to Grignard reagent at 15C in one portion. After stirring at 15C for 2 mm, the mixture was quenched by 200 mL of sat.NH4C1 and extracted with 200 mL of EtOAc. The separated organic phase was washed with 200 mL of brine, dried over Na2504, filtered and concentrated. The residue was purified by Combi-flash (0%-30% of EtOAc in PE/DCM(v/v=1/1)) to afford 36-5 (550 mg, 56%) as off-white solid, and 50 mg of 36-5 was delivered. ?H NMR (400 MHz,CDC13) 5.32-5.25 (m, 1H), 4.06-3.96 (m, 2H), 3.42-3.29 (m, 3H), 2.39-2.33 (m, 1H), 2.07-1.79(m, 6H), 1.77-1.60 (m, 7H), 1.5 1-1.38 (m, 1OH), 1.35-1.21 (m, 4H), 1.16-1.01 (m, 8H), 0.97-0.90(m, 4H), 0.85 (t, J = 7.4 Hz, 3H), 0.71-0.66 (m, 3H). LCMS Rt = 1.212 mm in 2 mmchromatography, 30-9OAB_2MIN_E.M, MS ESI calcd. for C31H5102 [M+H-H2Oj 455, found455., 1768-64-5

As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

Reference£º
Patent; SAGE THERAPEUTICS, INC.; SALITURO, Francesco, G.; ROBICHAUD, Albert, Jean; MARTINEZ BOTELLA, Gabriel; HARRISON, Boyd, L.; (157 pag.)WO2017/7840; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLES 57 TO 78; [00244] The procedures of Scheme E (General Procedure A) or Scheme F (General Procedure B) were employed to prepare the Examples 57 to 78 compounds.; Alkylation of Indazoles, General Procedure A; [00242] Shell vials were charged with methyl 3-(lH-indazol-5-yl)-2,2-dimethyl-3- phenylpropanate (150 mg, 0.49 mmol) in 2 mL THF and NaH (69 mg of 60% oil immersed, 1.8 mmol) was added under N2. After foaming subsided (about 10 min), the alkylating agent (2.24 mmol, 4.6 equiv) was added neat and the reactions were heated to reflux for 16 hr. The reactions were cooled, concentrated by rotary evaporation, diluted with 2 mL DMSO, 1 mL MeOH, and 1 mL 5M NaOH and heated for another 16 hr. The crude N-alkylated acids were purified by HPLC and lyophilized to give pure acids which were confirmed by LC-MS and then coupled to a Z-Za-NH2 amine using General Coupling Method A. The alkylation reactions gave mixtures of the N-I and N-2 alkylated indazoles (typically in a 1 : 1-3: 1 ratio favoring N-I) which could be separated by HPLC at the acid stage (and coupled independently) or separated at the final amide stage after coupling.

1768-64-5, As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/57856; (2008); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

Intermediate 18A (4-Amino-5-bromopyrrolo[2,l-fj[l ,2,4]triazin-7-yl)(tetrahydro-2/ -pyran-4-yl)methanol In a 50 l. three-necked flask equipped with a condenser, a thermometer and a dropping funnel, which was purged with argon, a Gri uard reagent was prepared from magnesium turnings (484 mg, 19.9 mmol) and 4-chlorotetrahydropyrane (2.4 g, 19.9 mmol) in dry THF (14 mL). To this solution was added at 0C a suspension of Intermediate 16A (1.2 g, 3.98 mmol) in THF (20 mL), and the reaction mixture was allowed to stir for 1 h at room temperature. It was then quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate (2 x 50 mL). The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC (method 3). Yield: 0.5 g (38% of th.). LC-MS (method 6): R, = 0.66 min; MS (ESIpos): m/z (%) = 327.0 (100) [M+H]+, MS (ESIneg): m/z (%) = 325.1 (100) [M-H]~

1768-64-5, 1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Bayer Pharma Aktiengesellschaft; KLAR, Juergen; VOEHRINGER, Verena; TELSER, Joachim; LOBELL, Mario; SUessMEIER, Frank; LI, Volkhart Min-Jian; BOeTTGER, Michael; GOLZ, Stefan; LANG, Dieter; SCHLEMMER, Karl-Heinz; SCHLANGE, Thomas; SCHALL, Andreas; FU, Wenlang; WO2013/4551; (2013); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A suspension of intermediate A (O. lg, 0.47mmol), 4-chlorotetrahydro-2H-pyran (leq) and potassium carbonate (2eq) in DMF (3mL) was stirred at 80C for 18h. LC-MS indicated that the reaction was not complete so further 4-chlorotetrahydro-2H-pyran (leq) and potassium carbonate (leq) were added and the mixture stirred at 80C for 24h. Further 4- chlorotetrahydro-2H-pyran (2eq) and potassium carbonate (2eq) were again added and the mixture stirred at 80C for 72h. After cooling to rt, the mixture was treated with H20 and extracted with dichloromethane. The organic phase was collected and dried using a hydrophobic frit then concentrated in vacuo. The resultant residue was purified by prep. HPLC to give the title product. 1H NMR (d6-DMSO) delta 9.77 (s, 1H), 8.90 (s, 1H), 8.02 (s, 1H), 7.61 (s, 1H), 4.84 (s, 1H), 4.02 (dd, 2H), 3.84 (s, 3H), 3.58 (t, 2H), 2.20 (td, 2H), 1.90 (dd, 2H); LC-MS method B, (ES+) 300, RT = 6.36 min.

1768-64-5, The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; CELLZOME LIMITED; HARRISON, Richard, John; OXENFORD, Sally; HOBSON, Andrew; RAMSDEN, Nigel; MILLER, Warren; WO2011/134831; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

1768-64-5, 4-Chlorotetrahydropyran is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 7 Preparation of 1-(4-tetrahydropyranyl)but-1-en-3-one 10.8 g (400 mmol) of Mg turnings are introduced into 30 ml of tetrahydrofuran containing a catalytic amount of iodine, and 5 ml of 4-chlorotetrahydropyran are added. The mixture is warmed to 50 C., and 45.2 g (375 mmol) of 4-chlorotetrahydropyran, dissolved in 120 ml of tetrahydrofuran, are added dropwise at such a rate that the internal temperature does not exceed 70 C. The mixture is stirred for a further 1 hour and subsequently cooled to room temperature. 42.4 g (375 mmol) of 1-(dimethylamino)but-1-en-3-one are added dropwise to the stirred mixture at such a rate that the reaction temperature does not exceed 30 C. The mixture is subsequently stirred for a further 2 hours and hydrolyzed, and the pH of the solution is adjusted to exactly 7. The phases are separated, and the aqueous phase is extracted several times with 200 ml of ethyl acetate or methyl tert.-butyl ether, dried and subjected to fractional distillation, to give 42.0 g (75%) of 1-(4-tetrahydropyranyl)but-1-en-3-one of boiling point 93 to 95 C./5 mmHg.

1768-64-5, 1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; BASF Aktiengesellschaft; US5221753; (1993); A;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

2-Propyl-lH-imidazo[4,5-c]quinolin-l-ol (0.4 g, 1.8 mmol), 4- chlorotetrahydropyran (0.4 g, 3.3 mmol), and l,8-diazabicyclo[5.4.0]undec-7-ene (0.4 g, 2.6 mmol) were combined in a pressure vessel. The vessel was sealed and then heated in an oven at 120 0C for 22 hours. The reaction was repeated on a larger scale (x8). The small and larger scale reaction mixtures were combined and then partitioned between dichloromethane (150 mL) and saturated aqueous sodium carbonate (25 mL). The organic layer was separated, washed with water (3 x 25 mL), dried over potassium carbonate, filtered, and then concentrated under reduced pressure to provide 4.8 g of crude product as a brown oil. This material was purified by column chromatography (silica gel eluted with 5% methanol in dichloromethane containing 5 mL of ammonium hydroxide per liter of dichloromethane) to provide 0.98 g of 2-propyl-l-(tetrahydro-2//-pyran-4-yloxy)-l/-r- imidazo[4,5-c]quinoline as a yellow oil. HRMS (ESI) calcd for Ci8H2IN3O2 + H+: 312.1712, found 312.1712.

1768-64-5, 1768-64-5 4-Chlorotetrahydropyran 137202, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2007/75468; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.

4-Chlorotetrahydropyran (650 muL, 6.0 mmol) was dissolved in THF (6 mL). Magnesium turnings (2.0 g, 80.7 mmol) was added to the mixture followed by methyl iodide (14 muL, 230 mumol). The mixture was stirred at 30 C. for 10 minutes and additional 4-chlorotetrahydropyran (9.3 g, 77 mmol) diluted in THF (60 mL) was added dropwise. 2.0M Isopropylmagnesium chloride in THF (2.0 mL) was added and the mixture was stirred overnight at 30 C. The mixture was cooled to room temperature to give a grey slurry of 0.8M 4-tetrahydropyranmagnesium chloride in THF., 1768-64-5

As the paragraph descriping shows that 1768-64-5 is playing an increasingly important role.

Reference£º
Patent; STANGELAND, Eric; SCHMIDT, Jane; SAITO, Daisuke Roland; HUGHES, Adam; PATTERSON, Lori Jean; US2011/21597; (2011); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics