Réaction #81273

Équation de réaction

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

Rendement 98.4%

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

Rendement 98.4%

Solvants

N,N-dimethylacetamide

N,N-dimethylacetamide

water

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source