Lithium hydroxide, monohydrate → HCID 67192009, compound

Participants

Reaction Conditions

Reaction Steps

3-Cyclopentyl-2-(1,1-dioxo-2,3-dihydro-benzo[b]thiophen-5-yl)-propionic acid methyl ester (184 mg, 0.57 mmol) was dissolved in ethanol (4 mL) and treated with a solution of lithium hydroxide monohydrate (34 mg, 1.43 mmol) in water (1.5 mL) at 25° C. It was stirred at 25° C. until the starting material was all consumed by TLC (˜1 hr). The reaction was then concentrated in vacuo to remove the ethanol. The remaining aqueous layer was then acidified to pH=2 with an aqueous 1N hydrochloric acid solution. This was then extracted with ethyl acetate (3×20 mL), the organic layers combined and dried over magnesium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-(1,1-dioxo-2,3-dihydro-benzo[b]thiophen-5-yl)-propionic acid (114 mg, 65%) as a white solid: EI-HRMS m/e calcd for C16H20O4S (M+) 308.1082, observed 308.1075.

Provenance & Evidence