Methanol → HCID 59350816, compound

Participants

Reaction Steps

To a solution of {6-fluoro-4-[hydroxy-(4-methanesulfonyl-phenyl)-methyl]-naphthalen-2-yl}-acetic acid methyl ester (90 mg, 0.23 mmol) in methanol (5 mL) was added 3 drops of concentrated sulfuric acid. The mixture was heated at reflux overnight. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and water. The collected organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 0-40% ethyl acetate in hexane) gave {6-fluoro-4-[(4-methanesulfonyl-phenyl)-methoxy-methyl]-naphthalen-2-yl}-acetic acid methyl ester (37.6 mg, 39%) as a clear oil. MS (ESI+) cald. for C22H21FO5S [(M+H)+] 416, obsd. 417.

Provenance & Evidence