(R)-4-Benzyl-2-oxazolidinone → (R)-4-Benzyl-3-pent-4-enoyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of (R)-4-benzyloxazolidin-2-one (2.242 g, 12.652 mmol) in 30 mL of THF, was added n-BuLi (5.6 mL, 13.917 mmol, 2.5 M in hexane). The resulting mixture was stirred at −78° C. under N2 for 15 min and then pent-4-enoyl chloride (1.500 g, 12.652 mmol) was added. After stirring at −78° C. for 1 h the reaction was warmed to room temperature under N2 and stirred overnight. The reaction mixture was quenched with 60 mL of aqueous NH4Cl solution and extracted with dichloromethane (50 mL×3). The combined organic extracts were dried, filtered, and concentrated under reduced pressure. The product was isolated by Flash column chromatography (silica gel) eluting with 0-30% ethyl acetate/hexanes to give the title compound as colorless oil (2.146 g, 65% yield). GC-MS: tR=4.2 min; m/z 259 (M+).

Provenance & Evidence