Citric Acid → methyl 4-[(2-phenyl-1H-indol-1-yl)methyl]benzoate

Participants

Reaction Steps

A mixed solution of 2-phenylindole (4.2 g, 21.7 mmol) and sodium hydride (60% in oil, 0.96 g, 24 mmol) in tetrahydrofuran (90 mL) and N,N-dimethylformamide (10 mL) was stirred under ice-cooling for 20 min. Methyl 4-bromomethylbenzoate (5.0 g, 21.8 mmol) was added to the reaction mixture, and the mixture was stirred at room temperature for 18 hr. Aqueous citric acid solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract washed with aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:10-1:5-1:2) to give the title compound (2.8 g, yield 38%) as a pale-yellow oil. MS: m/z 342 (MH+).

Provenance & Evidence