Sodium Hydroxide → 6-Chloro-7-(4-(6-(3,4-dichlorophenyl)pyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylic acid

Participants

Reaction Steps

To a solution of ethyl 6-chloro-7-(4-(6-(3,4-dichlorophenyl)pyridin-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (0.051 g, 0.085 mmol) in 3:1 v/v THF/ethanol (1 ml) was added 1M sodium hydroxide (0.20 ml, 0.20 mmol), and the reaction was stirred for 16 hours. The reaction was concentrated, taken up in water, and acidified with 1M hydrochloric acid. The reaction was extracted twice with EtOAc, and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by silica gel preparative thin-layer chromatography, eluting with 95:5:1 DCM/MeOH/glacial acetic acid to yield the desired compound (0.032 g, 0.056 mmol, 66% yield). MS (apci) m/z=569.0 (M+H).

Provenance & Evidence