반응 #81268

반응 방정식

water

potassium t-butoxide

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

methyl 4-(1-hydroxy-1-methylethyl)-2-methoxymethylimidazole-5-carboxylate

→

title compound

수율 76.5%

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

수율 76.5%

용매

N,N-dimethylacetamide

N,N-dimethylacetamide

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was first stirred at room temperature for 4 hours
2. 2
   workup.WAITat 50° C. for a further 2 hours
3. 3
   추출extracted with ethyl acetate
4. 4
   건조The extract was dried 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

194 mg of potassium t-butoxide were added, whilst ice-cooling, to a solution of 359 mg of methyl 4-(1-hydroxy-1-methylethyl)-2-methoxymethylimidazole-5-carboxylate [prepared as described in Preparation 42(v)] in 5 ml of N,N-dimethylacetamide, and the resulting mixture was stirred for 15 minutes. An the end of this time, a solution of 1.32 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 10 ml of N,N-dimethylacetamide was added. The mixture was first stirred at room temperature for 4 hours and then at 50° C. for a further 2 hours. The reaction mixture was then mixed with water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 848 mg of the title compound as crystals, melting at 120°-137° C. (with decomposition).

출처