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

HRID 377669노트

반응식

HRID 377669 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-chloro-phenyl)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 1 M) 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-efbb07d541ac4d689b203ffd0416fe1f
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06028091

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