Реакция #65271

Уравнение реакции

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

tetrahydrofuran

hydride

→

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

Растворители

toluene

Условия реакции

Обработка

1. 1
   Температураto slowly warm to room temperature
2. 2
   ДругоеThe reaction was quenched
3. 3
   workup.ADDITIONby pouring
4. 4
   Экстракцияthe product was extracted into methylene chloride
5. 5
   Промывкаthe organic extracts were washed with water, 5% sodium carbonate solution and brine
6. 6
   ДругоеCrystallization from ethanol/water

Методика

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.

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