تفاعل #81268

معادلة التفاعل

water

potassium t-butoxide

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

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

→

title compound

المردود 76.5%

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

المردود 76.5%

المذيبات

N,N-dimethylacetamide

N,N-dimethylacetamide

ظروف التفاعل

المعالجة

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
   استخلاصextracted with ethyl acetate
4. 4
   تجفيفThe extract was dried over anhydrous magnesium sulfate
5. 5
   أخرىthe solvent was removed by distillation under reduced pressure
6. 6
   أخرىThe resulting residue was purified by column chromatography through silica gel
7. 7
   workup.ADDITIONby volume mixture of hexane and ethyl acetate as the eluent

الإجراء التجريبي

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).

المصدر