Acetonitrile → HCID 18989226, compound

Participants

Reaction Steps

Sodium hydride (1.1 g of a 80% dispersion in mineral oil), methyl 1H-indole 4-carboxylate (5.46 g) and anhydrous acetonitrile were mixed under an inert atmosphere at 0° C. and stirred at room temperature for an hour. Methanesulphonyl chloride (1.8 g) was added at 0° C. and the mixture stirred at room temperature for 18 hours. Methanol and then water were then added and the mixture extracted with dichloromethane. The organic phase was washed with 2N hydrochloric acid, water, 1M sodium carbonate and water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by column chromatography eluting with ethyl acetate/hexane obtaining methyl 1-(methylsulphonyl)indole-4-carboxylate (4.7 g) as a white solid, m.p. 102°-104° C.

Provenance & Evidence