Iodine → (3-(Benzyloxy)cyclobutyl)methanol

Participants

Reaction Steps

A tetrahydrofuran solution of 3-(benzyloxy)cyclobutanecarboxylic acid (2.5 gm, 11.36 mmol) was added to a solution of sodium borohydride (0.52 gm, 13.63 mmol) in tetrahydrofuran. Iodine (1.44 gm, 5.68 mmol) in tetrahydrofuran solution was added to solution at 0° C., after about 15 minutes, and the mixture was stirred at room temperature for about 2 hours. It was quenched with dilute hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with dilute sodium hydroxide solution and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to get the title compound.

Provenance & Evidence