Dichloroacetic Acid → 4-Phenyl-5-(4-methylthiophenyl)-1-(alpha-ethoxyethyl)imidazole

Participants

Reaction Steps

A mixture of 12.0 g (0.045 mole) of 4-phenyl-5-(4-methylthiophenyl)-1H-imidazole, 6.7 g (0.052 mole) of dichloroacetic acid and 24.6 g (0.34 mole) of ethyl vinyl ether in 485 ml of toluene was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature and was then stirred overnight with 130 ml of 25% aqueous sodium hydroxide. The organic layer was separated and the aqueous layer was extracted with ether (2X). The organic fractions were combined, washed with brine and dried over anhydrous potassium carbonate. Removal of the solvent under vacuum afforded 15.3 g of an oil. The product was used in the subsequent reaction without purification.

Provenance & Evidence