Ethyl Acetate → HCID 53697912, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension containing [(4-methoxyphenyl)methyl]triphenylphosphonium bromide (8.3 g, 0.020 mol) in dry tetrahydrofuran (50 ml) at -20° C. under a nitrogen atmosphere was treated with a solution containing n-butyl lithium (14.3 ml of 1.4M; 0.020 mol) in hexane. The resulting deep-red solution was stirred at -20° C. for 20 minutes and was allowed to warm to room temperature. Stirring was maintained for an additional 20 minutes and the solution was cooled to -20° C. The cooled solution was treated with a solution of 1-(1H-imidazol-1-yl)-3-[(4-methoxyphenyl)methoxy]-2-propanone (Example 1c; 2.6 g, 0.010 mol) in dry tetrahydrofuran (20 ml) and the resulting mixture was stirred at room temperature for 14 hours. Ethyl acetate (500 ml) was added to the mixture and the resulting mixture was washed with water (3×150 ml) and dried over sodium sulfate. The solvent was evaporated off under reduced pressure to yield a crude product which was purified by column chromatography (silica gel, 30% hexane in chloroform) to give an isomeric mixture of E- and Z-1-[3-(4-methoxyphenyl)-2-[[(4-methoxyphenyl)methoxy]methyl]-2-propenyl]-1H-imidazole as a pale-yellow oil having the following structural characteristics:

Provenance & Evidence