Ethyl Acrylate → 2,3-dihydro-1-oxo-7-methoxy-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole

HRID 22286

反応式

HRID 22286 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14]CC)=O)=[CH:6]2.[H-].[Na+].[CH2:19]([O:21][C:22](=[O:25])[CH:23]=[CH2:24])[CH3:20]>C1(C)C=CC=CC=1>[O:14]=[C:12]1[C:7]2=[CH:6][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:9]=3[N:8]2[CH2:24][CH:23]1[C:22]([O:21][CH2:19][CH3:20])=[O:25]

参加物

5

反応物 3

HCID 8821Ethyl Acrylate2 回HCID 20926Ethyl 5-methoxyindole-2-carboxylateHCID 24758Sodium hydride2 回

生成物 1

HCID 199278602,3-dihydro-1-oxo-7-methoxy-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A stirred solution of ethyl 5-methoxy-indole-2-carboxylate (30 g, 137 mmol) in 1.5 L of toluene under N2 was treated with sodium hydride (6.7 g of 60% in oil, 167 mmol) and ethylacrylate (16.3 ml, 150 mmol). The mixture was heated to reflux. After 3 hours (hr), additional ethyl acrylate (3 ml) and sodium hydride (3.3 g) were added. After a total of 8 hr, the starting material was consumed completely and the mixture was quenched with ethanol and treated with water and dilute HCl and methylene chloride. The organic layer was washed with brine, dried and concentrated to give 2,3-dihydro-1-oxo-7-methoxy-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole, which was used directly in the next step.

後処理

  1. temperatureThe mixture was heated to reflux
  2. customAfter a total of 8 hr, the starting material was consumed completely
  3. customthe mixture was quenched with ethanol
  4. additiontreated with water and dilute HCl and methylene chloride
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-ae3267b8cb1e4db9854b509f3b09ea44
出典データセット
uspto-grants-1995_06
特許番号
US05428043

関連ノート

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