1,2-Dimethoxyethane → N-(2-(3-Formyl-2,5-dimethyl-1H-pyrrol-1-yl)ethyl)acetamide

Participants

Reaction Conditions

Reaction Steps

123 ml (1.34 mol) of phosphoryl chloride are added dropwise in the course of 30 minutes at 0° C. to 750 ml of 1,2-dimethoxyethane and 109 ml of dimethyl formamide. The mixture is stirred for a further 30 minutes at 0° C., and, in the course of 45 minutes at 0° C., 180 g (1 mol) of N-(2-(2,5-dimethyl-1H-pyrrolyl)ethyl)acetamide are introduced. After 10 minutes at 0° C., the mixture is allowed to warm to 10° C., stirred for 1 h at 10° C. and hydrolysed by pouring in a solution of 250 g of sodium hydroxide in 920 ml of water in the course of 2 h at 20° C. to the reaction mixture. The resulting reaction mixture is filtered, the organic phase is isolated and the water phase is extracted twice, each time with 370 ml of 1,2-dimethoxyethane. The organic phases are combined and substantially concentrated in vacuum. After addition of 250 ml of toluene, the mixture is concentrated to dehydrate it, 1 l of ethyl acetate is added and the mixture is filtered over silica gel and charcoal, crystallised and dried.

Provenance & Evidence