Реакция #81197

Уравнение реакции

sodium chloride

sodium hydride

4-acetyl-2-butylimidazole-5-carbonitrile

t-butyl 4'-(bromomethyl)biphenyl-2-carboxylate

→

title compound

Выход 56.5%

4-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butylimidazole-5-carbonitrile

Выход 56.5%

Растворители

N,N-dimethylacetamide

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe resulting mixture was stirred at 55° C. for 2.5 hours
2. 2
   Экстракцияwas then extracted with ethyl acetate
3. 3
   ПромывкаThe extract was washed with water
4. 4
   Сушкаdried over anhydrous magnesium sulfate
5. 5
   Другоеthe solvent was removed by distillation under reduced pressure
6. 6
   ДругоеThe resulting oily residue was purified by column chromatography through silica gel

Методика

0.192 g of sodium hydride (as a 55% w/w dispersion in mineral oil) was added to a solution of 0.843 g of 4-acetyl-2-butylimidazole-5-carbonitrile [prepared as described in Preparation 24(i)] in 17 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 20 minutes. 1.68 g of t-butyl 4'-(bromomethyl)biphenyl-2-carboxylate was then added, and the resulting mixture was stirred at 55° C. for 2.5 hours. At the end of this time, an aqueous solution of sodium chloride was added to the mixture, which was then extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting oily residue was purified by column chromatography through silica gel, using 4:1 and 2:1 by volume mixtures of hexane and ethyl acetate as the eluent, to afford 1.14 g of the title compound as a viscous oil.

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