N-bromobutanimide → Ethyl acetate hexane

Participants

Reaction Steps

N-Bromosuccinimide (1,2 g) and diethylaminosulphur trifluoride (1,2 g) are added to a solution of the pivaloyl ester (49) (2 g) in dichloromethane (100 ml) at 0° C. After 1 hour, saturated sodium bicarbonate is added. The dichloromethane layer is dried (MgSO4), filtered and evaporated. The β-fluoropyranoside (50) is purified by silica gel column chromatography eluting with ethyl acetate:hexane (2:8), (yield 45%).

Provenance & Evidence