Sodium Iodide → HCID 15015388, compound

Participants

Reaction Steps

A solution of 15 g. (0.057 mole) of 2-methyl-3-(4-methoxybenzoyl)indole in 120 ml. of DMF under nitrogen was treated with 1.36 g. (0.057 mole) of sodium hydride at 0° C. The mixture was allowed to warm to room temperature over a period of two hours and then treated with 20 ml. of chloromethyl trimethylsilane and a catalytic amount of sodium iodide and stirred at room temperature for about twelve hours. The solvent was removed by distillation in vacuo, the residue was mixed with 500 ml. of diethyl ether and the mixture filtered. The filtrate was taken to dryness, and the residue was chromatographed on silica gel, eluting with 30% ethyl acetate/hexane. The product, consisting of 16.5 g. of 2-methyl-3-(4-methoxybenzoyl)-1-trimethylsilylmethyl-1H-indole, was isolated as a light amber oil from the initial, more mobile fractions.

Provenance & Evidence