Potassium Hydroxide → HCID 69077442, compound

Participants

Reaction Steps

A solution of 3-(4-{3-[(cyclopropyl-methyl-amino)-methyl]-phenylethynyl}-phenyl)-but-2-enoic acid ethyl ester (Intermediate 93, 0.17 g, 0.46 mmol) in ethanol (3 mL) and tetrahydrofuran (3 mL) was treated with a 3.4M solution of potassium hydroxide (1 mL, 3.4 mmol) and the resulting reaction mixture was stirred at ambient temperature for 36 h. The reaction mixture was extracted with diethyl ether, and the aqueous phase was neutralized with 10% aqueous hydrochloric acid and evaporated to a solid. The solid was subjected to flash column chromatography using ethyl acetate as the eluent to afford the title product as a white solid (0.05 g, 32%). 1H NMR (300 MHz, CDCl3): δ 7.49-7.43(m, 4H), 7.32-7.20(m, 4H), 5.93(s, 1H), 3.70(s, 2H), 2.29(s, 3H), 2.17 (s, 3H), 1.76-1.73(m, 1H), 0.50-0.48(m, 4H).

Provenance & Evidence