Imidazole → Ethyl 2-[o-(1-imidazolylmethyl)phenoxy]propionate

Participants

Reaction Steps

To a suspension of 5.7 g of 50% sodium hydride in 200 ml of dry dimethylformamide was added slowly 8.0 g of imidazole at room temperature, and then the mixture was stirred for 30 minutes. A solution of 34.1 g of ethyl 2-(o-bromomethylphenoxy)propionate in 50 ml of dry dimethylformamide was added to the mixture at room temperature over a period of 1 hour, and then the reaction mixture was stirred at the same temperature for 1 hour. After removal of the solvent under vacuum, 150 ml of dichloromethane was added to the residual oil and the solution was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residual oil was chromatographed on silica gel using dichloromethane-ethanol (20:1 by volume) to give 15 g of ethyl 2-[o-(1-imidazolylmethyl)phenoxy]propionate as colorless needles. M.P.: 84°-85° C.

Provenance & Evidence