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

HRID 376742

反応式

HRID 376742 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8895Cupric acetate触媒HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b09a58324de647c7a97eb5a3c7ad5f03
出典データセット
uspto-grants-2000_02
特許番号
US06022379

関連ノート

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