Water → HCID 22915511, compound

Participants

Reaction Steps

To a solution in 2-propanol (30 mL) of 4-carboethoxy-5-[4-(4-cyanophenyl)phenoxy]pentanoic acid tert-butyl ester (0.9 g), prepared in step 1, was added aqueous 1M lithium hydroxide (8.6 mmol) and water (5 mL) to form a clear solution, and the reaction mixture was stirred for 3 hours. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted twice with ethyl ether and once with ethyl acetate. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (4% methanol-dichloromethane) provided 3-carboxy-5-[4-(4-cyanophenyl)phenoxy]pentanoic acid tert-butyl ester (0.62 g).

Provenance & Evidence