Lithium Hydroxide → HCID 22467935, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionic acid methyl ester (3.32 g, 9.26 mmol) in tetrahydrofuran (12 mL) was treated with a 0.8M aqueous lithium hydroxide solution (12 mL). The resulting reaction mixture was stirred at 25° C. for 24 h, at which time, thin layer chromatography indicated the presence of starting material. The reaction mixture was then heated at 80° C. for 18 h. The reaction mixture was then allowed to cool to 25° C. and concentrated in vacuo to remove tetrahydrofuran. The residue was acidified to pH=2 with a 10% aqueous hydrochloric acid solution and then extracted with ethyl acetate (2×150 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 3/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionic acid (1.74 g, 55%) as a white foam: mp 63-64° C.; EI-HRMS m/e calcd for C24H24O2 (M+) 344.1776, found 344.1770.

Provenance & Evidence