反应 #65271

反应方程式

5-carboxymethyl-1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazole

tetrahydrofuran

hydride

→

1-(2-chlorophenyl)methyl-5-hydroxymethyl-2-propylthio-1H-imidazole

溶剂

toluene

反应条件

后处理

1. 1
   温度to slowly warm to room temperature
2. 2
   其他The reaction was quenched
3. 3
   workup.ADDITIONby pouring
4. 4
   萃取the product was extracted into methylene chloride
5. 5
   洗涤the organic extracts were washed with water, 5% sodium carbonate solution and brine
6. 6
   其他Crystallization from ethanol/water

实验过程

A solution of 5-carboxymethyl-1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazole (3.74 g, 11.5 mmol) in dry tetrahydrofuran (50 ml) was cooled to -78° C. under argon, and a solution of diisobutyl alumninum hydride in toluene (30 ml of 1M) was added dropwise. The mixture was stirred at -78° C. for 1.5 hours, then allowed to slowly warm to room temperature. The reaction was quenched by pouring onto iced dilute acetic acid, the product was extracted into methylene chloride and the organic extracts were washed with water, 5% sodium carbonate solution and brine. The dried, concentrated product was a light tan solid (3.32 g). Crystallization from ethanol/water gave 1-(2-chlorophenyl)methyl-5-hydroxymethyl-2-propylthio-1H-imidazole; mp 98°-101° C.

来源