Diisobutylaluminum hydride → 5-(Hydroxymethyl)-1H-benzimidazole

HRID 398349

反応式

HRID 398349 の反応式
C([O:3][C:4]([C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][NH:12][C:8]=2[CH:7]=1)=O)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[OH:3][CH2:4][C:6]1[CH:14]=[CH:13][C:9]2[N:10]=[CH:11][NH:12][C:8]=2[CH:7]=1

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 13505555Ethyl 1H-benzimidazole-6-carboxylate

生成物 1

HCID 135055565-(Hydroxymethyl)-1H-benzimidazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a cooled (0° C.) suspension of ethyl-benzimidazole-5-carboxylate (4.76 g, 25 mmol) in CH2Cl2 (100 mL) was added a 1 M solution of DIBAL in CH2Cl2 (100 mL) and the mixture was stirred for 4 h. The reaction was quenched by the sequential addition of MeOH (8 mL), 1 M NaOH (16 mL), and 30% sodium potassium tartrate (40 mL). The mixture was warmed to RT and filtered, and the solid residue was washed with CH2Cl2. The filtrate was concentrated in vacuo to afford the title compound as a brown solid:

後処理

  1. temperatureTo a cooled
  2. customThe reaction was quenched by the sequential addition of MeOH (8 mL), 1 M NaOH (16 mL), and 30% sodium potassium tartrate (40 mL)
  3. filtrationfiltered
  4. washthe solid residue was washed with CH2Cl2
  5. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-2ed67267f49b4afa92a5a77e5d9340aa
出典データセット
uspto-grants-2003_08
特許番号
US06610692B1

関連ノート

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