Potassium Carbonate → Methyl 5-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate

Participants

Reaction Steps

A solution of 2-(imidazol-1-yl)acetaldehyde (2.8 g; 0.021 mmol), 4-(4-fluorophenethyl)-3-methoxycarbonylbenzyl triphenylphosphonium bromide (6.2 g; 0.01 mmol), potassium carbonate (2.8 g; 0.02 mmol) and 18 crown-6 (0.1 g; 0.37 mmol) in dichloromethane (100 ml) was stirred under argon atmosphere at ambient temperature overnight. After extraction and evaporation to dryness, the residue was purified by flash chromatography eluting with a mixture of dichloromethane/ethanol (98/2) to give methyl 5-[3-(imidazol-1-yl)prop-1-en-1-yl]-2-(4-fluorophenethyl)benzoate as a mixture of E and Z isomers.

Provenance & Evidence