Hydrochloric Acid → (4-Benzyloxy-6-fluoro-naphthalen-2-yl)-methanol

Participants

Reaction Conditions

Reaction Steps

To a slurry of lithium aluminum hydride (1.4 g, 37.4 mmol) in tetrahydrofuran (30 mL) was added a solution of 4-benzyloxy-6-fluoro-naphthalene-2-carboxylic acid methyl ester (5.8 g, 18.7 mmol) in tetrahydrofuran (30 mL) at 0° C. under a nitrogen atmosphere. After being heated at 60° C. for 1 hour under a nitrogen atmosphere, the resulting mixture was cooled to 0° C. and treated with 1 N hydrochloric acid to quench the reaction. The mixture was extracted with diethyl ether (50 mL×4). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give (4-benzyloxy-6-fluoro-naphthalen-2-yl)-methanol (4.9 g, 93%) as a white solid.

Provenance & Evidence