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

HRID 376739

Reaktionsgleichung

Reaktionsgleichung von HRID 376739
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-4cdfb3ea6fd1417dbb2b0b49ac16fede
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06022379

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