Benzyl Bromide → (2S,3S)-2-benzyl-3-hydroxy-gamma-butyrolactone

Participants

Reaction Conditions

Reaction Steps

Lithium hexamethyldisilazide (25 ml, 25 mmol) was loaded under argon gas in a reaction vessel. (S)-3-Hydroxy-γ-butyrolactone (1.012 g, 9.913 mmol) in THF (20 ml) was added thereto under cooling to −45° C. After stirring for 30 minutes at the same temperature, benzyl bromide (1.9 ml, 11.89 mmol) in THF (20 ml) was dropped thereto. After stirring for 4 hours at the same temperature, an aqueous saturated ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and condensed in vacuo. The residue was purified by silica gel chromatography to give (2S,3S)-2-benzyl-3-hydroxy-γ-butyrolactone (0.762 g, yield 40%).

Provenance & Evidence