Triethylamine → Oxan-4-ylmethyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

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 0° C. in 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 0° C. The reaction mixture was stirred for 30 minutes at 0° C. 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 (2×800 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.

Provenance & Evidence