Water → 2-Cyclopentyl-2-(4-(2-quinolylmethoxy)phenyl)acetic acid methyl ester

Participants

Reaction Steps

To a mixture of 4-(2-quinolylmethoxy)phenylacetic acid methyl ester (6.36 g; 20.7 mmol) in DMF (10 ml) at 0° C. was added in portions sodium hydride (60% dispersion in mineral oil) (840 mg; 21 mmol). The mixture was stirred at room temperature for 1 hour. It was then recooled to 0° C. and cyclopentyl bromide (2.38 ml, 22.0 mmol) was added dropwise. The resulting mixture was stirred at room temperature for 18 hours, and was then poured into water (50 ml). The product was extracted with ethyl acetate and purified by silica gel chromatography (hexane-ethyl acetate 3:1) to provide 5.5 g of 2-cyclopentyl-2-(4-(2-quinolylmethoxy)phenyl)acetic acid methyl ester.

Provenance & Evidence