Water → 2-(1-benzyl-1H-pyrrol-2-yl)-[1,4]-naphthoquinone

HRID 376742

반응식

HRID 376742 반응식
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[CH2:13]([N:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C(O)(=O)C.ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:13]([N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:3]1[C:4](=[O:11])[C:5]2[C:10]([C:1](=[O:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 85301,4-NaphthoquinoneHCID 749221H-Pyrrole, 1-(phenylmethyl)-

생성물 1

HCID 106150882-(1-benzyl-1H-pyrrol-2-yl)-[1,4]-naphthoquinone수율 18%

시약·촉매·용매 3

HCID 8895Cupric acetate촉매HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

3.16 millimol of 1,4-naphthoquinone were stirred with 25 millimol of N-benzylpyrrole and 3.16 millimol of copper acetate in 50 ml of acetic acid in a round-bottomed flask at room temperature for 1 hour. The reaction mixture was diluted with 300 ml of dichloromethane and the resulting mixture was then poured into a large volume of water (300 ml). The organic phase was then separated out and washed four times with 100 ml of water and finally with saturated aqueous NaCl solution. The resulting organic phase was dried over Na2SO4 and then concentrated under vacuum. The product 2-(1-benzyl-1H-pyrrol-2-yl)-[1,4]-naphthoquinone was thus isolated in a yield of 18% after purification by chromatography on a column of silica.

후처리

  1. customThe organic phase was then separated out and
  2. washwashed four times with 100 ml of water
  3. dry with materialThe resulting organic phase was dried over Na2SO4
  4. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-b09a58324de647c7a97eb5a3c7ad5f03
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022379

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