Hydrochloric Acid → [4-(4-Ethanesulfonyl-phenoxy)-6-fluoro-naphthalen-2-yl]-acetic acid

Participants

Reaction Steps

5 N lithium hydroxide (6 mL) was added to a solution of [4-(4-ethanesulfonyl-phenoxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester (64 mg, 0.16 mmol) in tetrahydrofuran (4 mL). After being stirred at room temperature overnight, the resulting mixture was acidified to pH 3 with 5 N hydrochloric acid, and then extracted with ethyl acetate (10 mL×2). The organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was precipitated from ethyl ester/petroleum ether (1:10) to give [4-(4-ethanesulfonyl-phenoxy)-6-fluoro-naphthalen-2-yl]-acetic acid (25 mg) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.84-7.90 (m, 3H), 7.65 (s, 1H), 7.57 (dd, J=9.85, 2.53 Hz, 1H), 7.33 (td, J=8.65, 2.65 Hz, 1H), 7.09-7.14 (m, 3H), 3.80 (s, 2H), 3.13 (q, J=7.33 Hz, 2H), 1.30 (t, J=7.45 Hz, 3H); MS cald. for C20H17FO5S 388, obsd. (ESI+) [(M+H)+] 389.

Provenance & Evidence