Imidazole → N-p-methoxybenzylimidazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 10.88 g (0.16 mol) of imidazole in 150 ml of dry DMF at 0° C. under argon was added 6.4 g (0.16 mol) of 60% NaH, and the mixture was stirred at 0° C. for 30 min and then at room temperature for 1 h. The mixture was cooled to 0° C., and 25 g (0.16 mol) of p-methoxybenzyl chloride was added, and the mixture was stirred at room temperature for 24 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between methylene chloride and water. The organic layer was dried over sodium sulfate, concentrated in vacuo to yield 35.6 g of a crude product which was purified by chromatography on silica (methylene chloride/methanol 9:1) to afford 25.3 g (84.2%) of 1-(p-methoxybenzyl)-imidazole.

Provenance & Evidence