Category: 1197-66-6

1197-66-6, 2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1. 1-(4-hydroxy-2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)ethanone To a stirred solution of ethoxyethene (1.84 g, 25.5 mmol) in THF (40 mL) was added tBuLi (16 mL, 25.6 mmol) at -78 C. The reaction mixture was slowly allowed to warm to 10 C. followed by addition of 2,2,6,6-tetramethyldihydro-2H-pyran-4(3H)-one (2 g, 12.8 mmol). The mixture was stirred for 16 h at room temperature. The reaction was quenched by the addition of HCl (3 mL) in aqueous methanol (20 mL, MeOH_H2O=1:1). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide the crude title compound as an off-white solid (1.2 g) which was used in the next step without further purification.

1197-66-6, The synthetic route of 1197-66-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Janssen Pharmaceutica NV; Ahmad, Ishtiyaque; Bakthavatchalam, Rajagopal; Battula, Sivaramakrishna; Gijsen, Henricus Jacobus, Maria; Wall, Mark; US2015/51225; (2015); 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.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

A 2 L RBF under light nitrogen flow was charged with 2,2,6,6-tetramethyldihydro-2H-pyran-4(3H)-one (1.00 equiv; 49.10 mL; 43.45 g), (a known compound which may be prepared as described in, for example, MAGNUS, P., et al., ?Synthesis of the ABCD-rings of the insecticidal indole alkaloid nodulisporic acid?, Tet. Lett., 1999, pp 6909-6912, Vol. 40) 2-methyl-THF (375.00 mL; 322.05 g) and DBU (76.67 mL; 77.67 g). The resulting mixture was stirred and cooled to about 2 C. with a water-ice bath. NfsulphF (1.20 equiv; 56.07 mL; 94.20 g) was introduced into a dropping funnel and the NfsulphF was then added to the reaction mixture over 20 minutes, with a light exotherm is observed. After complete addition, the water-ice bath was taken away and the temperature allowed to rise to room temperature. Precipitation was observed to start forming, resulting in a yellow suspension. The yellow suspension was stirred overnight at room temperature and yielded yield a brown suspension. [0249] To the brown suspension was slowly added water (1.12 L; 1.12 kg), with an observed exotherm. The resulting mixture was warmed 44 C., resulting in a multi-phase mixture with good separation (the organic layer was the top layer). The mixture was stirred for 20 minutes and the phases warm separated at about 44 C. The aqueous (orange colored) layer was returned to the RBF, and then extracted with 2-methyl-THF (185.00 mL; 158.88 g) by stirring 20 minutes at 44 C., then warm separating the resulting layers. The organic layers were then combined. Water (190.00 mL; 190.00 g) was added and the resulting mixture stir for 20 minutes, and the resulting layers warm separated at 44 C. The organic layer was then washed second time with water (190.00 mL; 190.00 g), with some white fluffy precipitation observed in the water layer. The organic layer was then evaporated on a rotavap at 45 C. The resulting biphasic residue included a thick brown bottom layer (129.17 g) and light colored material on top. To the residue was added HEPTANE 50% (a mixture of 50% n-heptane, 20% other heptane isomers and 30% methyl cyclohexane; 250.00 mL; 176.75 g), then acetonitrile (19.00 mL; 14.88 g). The resulting mixture was stirred firmly, the acetonitrile was observed to take up the oily layer, resulting in a biphasic system. The mixture was then stirred for 1 hour, the layers separated. The heptane layer was evaporated on a rotovap at 42 C. to yield the title compound as a residue (102.60 g) [0250] Actual Yield: 93.52% 102.60 g, 234.08 mmol [0251] Theoretical Yield: 100% 109.58 g, 250.00 mmol, 1197-66-6

As the paragraph descriping shows that 1197-66-6 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; KOLODZIEJCZYK, Krzysztof; Stappers, Alfred Elisabeth; Teleha, Christopher A.; Weerts, Koen Johan Herman; US2014/45789; (2014); 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.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

A. 2,2,6,6-Tetramethyl-tetrahydro-2H-pyran-4-ol, 10a (0297) (0298) A solution of 2,2,6,6-tetramethyloxan-4-one (190 mg, 1.22 mmol) and NaBH4 (93 mg, 2.5 mmol) in THF (4 mL) and methanol (2 mL) was stirred for 1 h at RT. The reaction was then quenched by the addition of 0.1 mL of water. The resulting mixture was concentrated. The residue obtained was purified by column chromatography on silica gel (EtOAc/petroleum ether (1:5-1:3 v/v)) to give the compound 10a. 1H-NMR (300 MHz, CDCl3) delta (ppm): 3.88-3.97 (m, 1H), 1.71-1.77 (m, 2H), 1.36-1.37 (m, 1H), 1.20-1.25 (m, 1H), 0.97-1.05 (m, 6H), 0.89-0.95 (m, 6H)., 1197-66-6

As the paragraph descriping shows that 1197-66-6 is playing an increasingly important role.

Reference£º
Patent; Janssen Pharmaceutica NV; Meegalla, Sanath; Huang, Hui; Player, Mark R.; (53 pag.)US2016/9662; (2016); 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.1197-66-6,2,2,6,6-Tetramethyl-2H-3,5,6-trihydropyran-4-one,as a common compound, the synthetic route is as follows.

Step I, i-(4-hydroxy2,2,6,64etrameihyItetrahydro4Hpyran-4y1)eihanone: To astirred solution of ethoyethene (184 g, 25.5 mmol) in THE (40 mE) was added t8J (16rnL, 25.6 mmoi) at -78 C. The reaction mixture was slowly allowed to warm to 10 Cfollowed by addition of 2 ,2,6,6-tetramethyldihydro-2H–pyran-4(3 [1)-one (2 g, 1 2.8 mmol).The mixture was stirred for 16 h at room temperature. The reaction was quenched by theaddition of HCI (3 mL) in aqueous methanol (20 mL, MeOR 1:1). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide the crude title compound as an off-white sob ci (1 .2 g) which was used in the next step without further purification., 1197-66-6

As the paragraph descriping shows that 1197-66-6 is playing an increasingly important role.

Reference£º
Patent; JANSSEN PHARMACEUTICA NV; BAKTHAVATCHALAM, Rajagopal; AHMAD, Ishtiyaque; BATTULA, Sivaramakrishna; GIJSEN, Henricus Jacobus Maria; VADIVELU, Saravanan; WALL, Mark; WO2015/23289; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics