Reaction #81283

Reaction equation

ethyl 4-(1-hydroxy-1-methylethyl)-2-ethoxymethylimidazole-5-carboxylate

ethyl 2-ethoxyethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate

potassium t-butoxide

4-[2-(t-butoxycarbonyl)phenyl]benzyl bromide

→

title compound

Yield 98.5%

Ethyl 1-{4-[2-(t-butoxycarbonyl)phenyl]phenyl}methyl-2-ethoxymethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate

Yield 98.5%

Conditions

Workup

1. 1
   Otherthe product was purified by column chromatography through silica gel using a 1:1
2. 2
   workup.ADDITIONby volume mixture of hexane and ethyl acetate as the eluent

Procedure

A procedure similar to that described in Example 82(a) was repeated, except that 315 mg of ethyl 4-(1-hydroxy-1-methylethyl)-2-ethoxymethylimidazole-5-carboxylate [prepared as described in Preparation 44(iii)], 145 mg of potassium t-butoxide and 510 mg of 4-[2-(t-butoxycarbonyl)phenyl]benzyl bromide were employed and the product was purified by column chromatography through silica gel using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to obtain 600 mg of the title compound as a syrup.

Source