Methanesulfonyl chloride → Oxan-4-yl methanesulfonate

To a solution of tetrahydro-2H-pyran-4-ol (2.5 g, 24.5 mmol) in DCM (40 mL) was added DIEA (6.40 mL, 36.7 mmol) at 0° C. and allowed to stir under nitrogen for 10 minutes. Methane sulfonyl chloride (2.18 mL, 28.1 mmol) was added slowly. The reaction was allowed to proceed for 1 hour at 0° C. The reaction was partitioned between 100 mL of DCM and 50 mL of 0.5 M hydrochloric acid. The layers were separated and the organic layer was then washed sequentially with water, saturated sodium bicarbonate, and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure and dried on high vacuum to afford tetrahydro-2H-pyran-4-yl methanesulfonate (4.4 g, 24.4 mmol, 99.7% yield).

1. waitto proceed for 1 hour at 0° C
2. customThe reaction was partitioned between 100 mL of DCM and 50 mL of 0.5 M hydrochloric acid
3. customThe layers were separated
4. washthe organic layer was then washed sequentially with water, saturated sodium bicarbonate, and brine
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customdried on high vacuum

ORD record

ord-a24a33f783bf487e86f1433d49acd51d

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962596B2