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

HRID 22286

반응식

HRID 22286 반응식
[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]

참가 물질

5

반응물 3

HCID 8821Ethyl Acrylate2회HCID 20926Ethyl 5-methoxyindole-2-carboxylateHCID 24758Sodium hydride2회

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ae3267b8cb1e4db9854b509f3b09ea44
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428043

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