1-Methyl-1H-Indole-4-Carboxylic Acid → 1-(1-Methyl-1H-indol-4-yl)ethanone

Participants

Reaction Steps

Methyl lithium (1.59M solution in ether; 13.8 ml) was added dropwise to a stirred cold (-65° to -55°) solution of 1-methyl-1H-indole-4-carboxylic acid (1.75 g) in dry THF (50 ml) under nitrogen and stirring was continued while the mixture warmed to 0° over 2 h. The reaction was then quenched with saturated ammonium chloride solution (50 ml) and the layers were separated. The aqueous layer was further extracted with dichloromethane (2×50 ml) and the combined organic layers were washed with brine (2×50 ml), dried and evaporated in vacuo. The residual solid (1.8 g) was purified by FCC eluting with dichloromethane to give the title compound (1.6 g), m.p. 63°-64°.

Provenance & Evidence