反応 #81170

反応方程式

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

sodium hydride

ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate

→

title compound

収率 79.9%

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

収率 79.9%

溶媒

N,N-dimethylformamide

N,N-dimethylformamide

ethyl acetate

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 2 hours
2. 2
   workup.WAITat 60° C. for 4 hours
3. 3
   洗浄the solution was washed three times with water
4. 4
   乾燥The solution was then dried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONafter which it was freed from the solvent by distillation
6. 6
   その他The residue was purified by column chromatography through silica gel
7. 7
   workup.ADDITIONby volume mixture of hexane and ethyl acetate as the eluent

実験手順

48 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) were added to a solution of 0.26 g of ethyl 4-(1-hydroxy-1-methylethyl)-2-propylimidazole-5-carboxylate (prepared as described in Preparation 9) in 5 ml of N,N-dimethylformamide, and the resulting mixture was stirred at room temperature for 30 minutes. A solution of 0.72 g of 4-[2-(trityltetrazol-5-yl)phenyl]benzyl bromide in 5 ml of N,N-dimethylformamide was then added, and the reaction mixture was stirred at room temperature for 2 hours and then at 60° C. for 4 hours. At the end of this time, it was dissolved in ethyl acetate and the solution was washed three times with water. The solution was then dried over anhydrous sodium sulfate, after which it was freed from the solvent by distillation. The 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 0.62 g of the title compound as an amorphous solid. This was crystallized from diisopropyl ether, to give the title compound as crystals, melting at 167°-168° C. (with decomposition).

出典