Oxalyl chloride → (6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl ester

Participants

Reaction Steps

A 0° C. solution of 6-benzyloxyindole (2.10 g, 9.41 mmol) in diethyl ether (20 mL) is treated with oxalyl chloride (1.02 mL, 11.8 mmol). The mixture is stirred for 2 hours while warming to room temperature. The mixture is cooled to −78° C. and sodium methoxide (5.41 mL, 4.35 M) is added. The mixture is warmed up to room temperature over 20 minutes and the reaction is quenched with water (10 mL). The resulting mixture is filtered to obtain the title compound (2.75 g, 95%) as a yellow solid. ES/MS m/e 310.0 (M+1), 308.0 (M−1).

Provenance & Evidence