반응 #81273

반응 방정식

potassium t-butoxide

4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide

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

ethyl acetate

→

title compound

수율 98.4%

Ethyl 2-ethoxymethyl-4-(1-hydroxy-1-methylethyl)-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

수율 98.4%

용매

N,N-dimethylacetamide

N,N-dimethylacetamide

water

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 2 hours
2. 2
   workup.STIRRINGshaken
3. 3
   기타The ethyl acetate layer was separated
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   기타The solvent was removed by distillation under reduced pressure
6. 6
   기타the resulting residue was purified by column chromatography through silica gel
7. 7
   workup.ADDITIONby volume mixture of hexane and ethyl acetate as the eluent

실험 절차

217 mg of potassium t-butoxide were added, whilst ice-cooling, to a solution of 450 mg of ethyl 2-ethoxyethyl-4-(1-hydroxy-1-methylethyl)imidazole-5-carboxylate [prepared as described in Preparation 44(iii)] in 5 ml of N,N-dimethylacetamide, and the mixture was stirred for 30 minutes. At the end of this time, a solution of 1.47 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 10 ml of N,N-dimethylacetamide was added dropwise to the mixture. The mixture was stirred at room temperature for 2 hours, after which it was mixed with ethyl acetate and water and shaken. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.2 g of the title compound as an amorphous powder.

출처