Tetrahydrofuran → (2-Fluoro-5-methylphenyl)methanol

Participants

Reaction Steps

A solution of 2-fluoro-5-methylbenzaldeyde (1.80 g, 12.3 mmol) in 3:1 tetrahydrofuran:methanol (82 ml total) at 0° C. was treated with sodium borohydride (0.93 g, 24.6 mmol). The reaction was slowly warmed to ambient temperature and stirred for about three hours. The reaction was quenched with water, transferred to a separatory funnel, and extracted with methylene chloride. The organic fraction was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was further purified by high performance liquid chromatography to yield 1.3 grams (76%) of a clear oil.

Provenance & Evidence