تفاعل #65271

معادلة التفاعل

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

tetrahydrofuran

hydride

→

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

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto slowly warm to room temperature
2. 2
   أخرىThe reaction was quenched
3. 3
   workup.ADDITIONby pouring
4. 4
   استخلاصthe product was extracted into methylene chloride
5. 5
   غسيلthe organic extracts were washed with water, 5% sodium carbonate solution and brine
6. 6
   أخرىCrystallization from ethanol/water

الإجراء التجريبي

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.

المصدر