Sodium borohydride → HCID 59350854, compound

Participants

Reaction Steps

To a solution of [6-fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid methyl ester (103.5 mg, 0.26 mmol) (example 2-1, 4th step) in methanol (3 mL) was added sodium borohydride (30 mg, 0.78 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight, and then partitioned between ethyl acetate and water. The collected organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 0-40% ethyl acetate in hexane) gave {6-fluoro-4-[hydroxy-(4-methanesulfonyl-phenyl)-methyl]-naphthalen-2-yl}-acetic acid methyl ester (90 mg, 86%) as a yellow oil. MS (ESI+) cald. for C21H19FO5S 402 [(M+H)+], obsd. 403.

Provenance & Evidence