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

HRID 273826ノート

反応式

HRID 273826 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-af8257320ee74762b2c21e9c5be23bf8
出典データセット
uspto-grants-1995_02
特許番号
US05387601

反応ノート

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