Triethylamine → HCID 58248246, compound

Temperature

0 °C

A solution of 4.86 g (55.18 mmol) of (R)-(−)-3-hydroxytetrahydrofuran in 55 mL of anhydrous DCM (1M) was cooled to 0° C. with an ice bath. Then 8.5 mL (60.7 mmol, 1.1 eq.) of triethylamine and 4.8 mL (60.7 mmol, 1.1 eq.) of methanesulfonyl chloride were added successively. The reaction mixture was stirred for 2 hours at 0° C. and quenched with a saturated solution of sodium bicarbonate (70 mL). The aqueous layer was extracted with DCM (50 mL). Then the organic layers were washed with water (2×50 mL), brine (50 mL) and dried over sodium sulfate. After filtration and concentration in vacuo, a yellowish oil (7.93 g, 86.4%) was obtained corresponding to the methanesulfonic acid(R)-(tetrahydrofuran-3-yl)ester.

1. customquenched with a saturated solution of sodium bicarbonate (70 mL)
2. extractionThe aqueous layer was extracted with DCM (50 mL)
3. washThen the organic layers were washed with water (2×50 mL), brine (50 mL)
4. dry with materialdried over sodium sulfate
5. filtrationAfter filtration and concentration in vacuo

ORD record

ord-411fc5c7e68a4089a098c80afdd54b6a

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124613B2