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

HRID 36993노트

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HRID 36993 반응식
C([CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:8]([S:18][CH2:19][CH2:20][CH3:21])=[N:7][CH:6]=1)(O)=O.[H-].[O:23]1CCCC1>C1(C)C=CC=CC=1>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][N:9]1[C:5]([CH2:4][OH:23])=[CH:6][N:7]=[C:8]1[S:18][CH2:19][CH2:20][CH3:21]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 166653HydrideHCID 193515541-(2-chlorophenyl)methyl-5-carboxymethyl-2-propylthio-1H-imidazole

생성물 1

HCID 152809451-(2-chlorophenyl)methyl-5-hydroxymethyl-2-propylthio-1H-imidazole

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
-78 °C

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.

후처리

  1. temperatureto slowly warm to room temperature
  2. customThe reaction was quenched
  3. additionby pouring
  4. extractionthe product was extracted into methylene chloride
  5. washthe organic extracts were washed with water, 5% sodium carbonate solution and brine
  6. customCrystallization from ethanol/water

출처 및 근거

ORD 기록
ord-04b73e6722314de49eb1948cfab9efec
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05418250

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