Benzyl Bromide → 4-Benzyloxy-1-butanol

Participants

Reaction Steps

To a solution of diol compound (4.51 g, 50 mmol) in dry THF (50 ml) was added 60% NaH (1.6 g, 43 mmol) at 0° C. After stirring for 2 hours, benzyl bromide (5.7 g, 33 mmol) was added dropwise and stirred for 15 hours. After the reaction was completed, ice-water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and filtered. The organic solvent was removed under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=10:1) to give the title compound (936 mg, yield: 16%).

Provenance & Evidence