p-Toluenesulfonic acid → 2-(1-pentyl-1H-pyrrol-2-yl)-[1,4]-naphthoquinone

HRID 376739

反応式

HRID 376739 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:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1)[CH2:14][CH2:15][CH2:16][CH3:17].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH2:13]([N:18]1[CH:22]=[CH:21][CH:20]=[C:19]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)[CH2:14][CH2:15][CH2:16][CH3:17]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 85301,4-NaphthoquinoneHCID 557117n-Pentylpyrrole

生成物 1

HCID 106614012-(1-pentyl-1H-pyrrol-2-yl)-[1,4]-naphthoquinone収率 26%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

6.32 millimol of 1,4-naphthoquinone and 3.16 millimol of N-pentylpyrrole were stirred in 50 ml of chloroform in a round-bottomed flask for 5 hours at room temperature, the reaction being catalysed by addition of a few milligrams of para-toluenesulphonic acid. The reaction medium was diluted with 50 ml of chloroform and then washed four times with 50 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-pentyl-1H-pyrrol-2-yl)-[1,4]-naphthoquinone was thus isolated, in the form of an oil, in a yield of 26% after purification by chromatography on a column of silica.

後処理

  1. washwashed four times with 50 ml of water
  2. dry with materialThe resulting organic phase was dried over Na2SO4
  3. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-4cdfb3ea6fd1417dbb2b0b49ac16fede
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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