Borane → Methyl 2-(4-fluorophenethyl)-5-hydroxymethylbenzoate

Participants

Reaction Steps

A mixture of 4-(4-fluorophenethyl)-3-methoxycarbonylbenzoic acid (16.5 g, 54.88 mmol), tetrahydrofuran (500 ml) and borane in tetrahydrofuran (1M. complex, 218 mls, 218 mmol) was stirred under an inert atmosphere at reflux for 6 hours. The reaction was cooled to ambient temperature and methanol (1 L) was added. It was then evaporated to dryness to give a dark oil which was purified by flash column chromatography using iso-hexane/ethyl acetate (1:1) as eluant to give, as a clear gum, methyl 2-(4-fluorophenethyl)-5-hydroxymethylbenzoate (13.10 g).

Provenance & Evidence