Reaktion #65271

Reaktionsgleichung

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

tetrahydrofuran

hydride

→

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto slowly warm to room temperature
2. 2
   SonstigeThe reaction was quenched
3. 3
   workup.ADDITIONby pouring
4. 4
   Extraktionthe product was extracted into methylene chloride
5. 5
   Waschenthe organic extracts were washed with water, 5% sodium carbonate solution and brine
6. 6
   SonstigeCrystallization from ethanol/water

Vorschrift

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.

Quelle