반응 #65271

반응 방정식

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

tetrahydrofuran

hydride

→

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

용매

toluene

반응 조건

후처리

1. 1
   온도to slowly warm to room temperature
2. 2
   기타The reaction was quenched
3. 3
   workup.ADDITIONby pouring
4. 4
   추출the product was extracted into methylene chloride
5. 5
   세척the organic extracts were washed with water, 5% sodium carbonate solution and brine
6. 6
   기타Crystallization from ethanol/water

실험 절차

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.

출처