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

HRID 260727ノート

反応式

HRID 260727 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-(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; mp 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-44be20f848c04eb7a676d5581a3d7efc
出典データセット
uspto-grants-1996_06
特許番号
US05530017

反応ノート

読み込み中…