With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.14774-37-9,Tetrahydropyran-4-methanol,as a common compound, the synthetic route is as follows.
Preparation 1; Methanesulfonic acid tetrahydropyran-4-ylmethyl ester; A solution of 90 g (774.8 mmol) of tetrahydropyran-4 -methanol and 129.6 mL (929.76 mmol, 1.2 eq.) of triethylamine in 775 mL of anhydrous DCM was cooled to 00C with in an ice bath. Methanesulfonyl chloride (66.2 mL, 852.28 mmol, 1.1 eq.) of was then added dropwise over 60 minutes while maintaining the temperature around O0C. The reaction mixture was stirred for 30 minutes at O0C and quenched with a saturated solution of sodium bicarbonate (800 mL) . The aqueous layer was extracted with DCM (800 mL) . The combined organic layers were washed with water (2 x 800 mL) , brine (800 mL) and dried over sodium sulfate. After filtration and concentration in vacuo, a yellowish solid (146.1 g, 97%) was obtained corresponding to the methanesulfonic acid tetrahydropyran-4-ylmethyl ester.IH NMR (400 MHz, DMSOd6): delta [ppm] 4.02 (d, 2H), 3.82 (m, 2H), 3.27 (t x d, 2H), 3.14 (s, 3H), 1.89 (m, IH), 1.55 (m, 2H), 1.21(q x d, 2H) .; Preparation 13; Methanesulfonic acid tetrahydropyran-4-ylmethyl ester; A solution of 90 g (774.8 mmol) of tetrahydropyran-4 -methanol and 129.6 mL (929.76 mmol, 1.2 eq.) of t?ethylamine m 775 mL of anhydrous DCM was cooled to 00C m an ice bath. Methanesulfonyl chloride (66.2 mL, 852.28 mmol, 1.1 eq.) was then added dropwise over 60 minutes while maintaining the temperature around 00C. The reaction mixture was stirred for 30 minutes at 00C and quenched with a saturated solution of sodium bicarbonate (800 mL) . The aqueous layer was extracted with DCM (800 mL) . The combined organic layers were washed with water (2 x 800 mL) , brine (800 mL) and dried over sodium sulfate. After filtration and concentration m vacuo, a yellowish solid (146.1 g, 97%) was obtained corresponding to the methanesulfonic acid tetrahydropyran-4-ylmethyl ester .IH NMR (400 MHz, DMSO-O6): delta [ppm] 4.02 (d, 2H), 3.82 (m, 2H), 3.27 (t x d, 2H), 3.14 (s, 3H), 1.89 (m, IH), 1.55 (m, 2H), 1.21 (q x d, 2H) ., 14774-37-9
14774-37-9 Tetrahydropyran-4-methanol 2773573, aTetrahydropyrans compound, is more and more widely used in various fields.
Reference£º
Patent; VIROCHEM PHARMA INC.; WO2007/143847; (2007); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics