Acetyl chloride → methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate

HRID 14222

反応式

HRID 14222 の反応式
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[Cl-].C([Al+]CC)C.[C:24](Cl)(=[O:26])[CH3:25]>ClCCl>[C:24]([C:7]1[C:8]2[C:13](=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:9]=2)[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]=1)(=[O:26])[CH3:25]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 16686102Diethyl aluminum chlorideHCID 21086134methyl 1-butyl-1H-indole-6-carboxylate

生成物 1

HCID 21086157methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Methyl 1-butyl-1H-indole-6-carboxylate (4.53 g) was dissolved in dichloromethane (25 ml). The mixture was cooled to 0° C. Diethyl aluminum chloride was added dropwise (29.5 mL) and the mixture was allowed to stir at 0° C. for 30 min. A solution of dichloromethane (25 mL) and acetyl chloride (2.1 mL) was added dropwise, and the mixture was stirred for 2 h at 0° C. The mixture was then partitioned between dichloromethane, water, and brine, dried over sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on silica gel using ethyl acetate/heptane (40/60) to give methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate (3.38 g). MS (ESI+) for C16H19N1O3+H1 m/z 274.14 (M+H)+.

後処理

  1. stirringthe mixture was stirred for 2 h at 0° C
  2. customThe mixture was then partitioned between dichloromethane, water, and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was chromatographed on silica gel

出典と根拠

ORDレコード
ord-bafabbc4e9f84e05a328917e3b643fdc
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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