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

HRID 273826노트

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HRID 273826 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-].C([Al+]CC(C)C)C(C)C.[O:32]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:32])=[CH:6][N:7]=[C:8]1[S:18][CH2:19][CH2:20][CH3:21]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 193515541-(2-chlorophenyl)methyl-5-carboxymethyl-2-propylthio-1H-imidazoleHCID 21225700Diisobutylaluminumhydride

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
-78 °C

실험 절차

A solution of 5-carboxymethyl-1-1-(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 aluminum 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; m.p. 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-af8257320ee74762b2c21e9c5be23bf8
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387601

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