Sulfuric Acid → HCID 20270201, compound

Participants

Reaction Steps

A solution of 4.55 g of ethyl p-hydroxybenzoate in 50 ml of dry dimethylformamide is treated with 1.31 g of 50% sodium hydride dispersion in mineral oil under nitrogen at 0°, stirred for 30 minutes at 0°, and then at room temperature for 15 minutes. A solution of 7.55 g of 3-(methanesulfonyloxymethyl)-N-(3-pyridyl)indole in 10 ml of dry dimethylformamide is added over 5 minutes and the reaction mixture is warmed at 50° for 18 hours. The reaction mixture is poured onto ice, made acidic with concentrated sulfuric acid and extracted with diethyl ether (4×40 ml). The aqueous phase is adjusted to pH=8 and is extracted with diethyl ether (3×100 ml). The organic extracts are washed with water (4×50 ml) and brine (1×50 ml) and dried over anhydrous sodium sulfate. Evaporation and chromatography on 100 g of silica with diethyl ether as the eluent yields 3-[(p-ethoxycarbonylphenoxy)methyl]-N-(3 -pyridyl)indole.

Provenance & Evidence