Diethyl Ether → 2-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 128748

Reaktionsgleichung

Reaktionsgleichung von HRID 128748
[C:1]1(=[O:18])[N:5]([CH:6]2[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]2)[C:4](=[O:13])[C:3]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:2]12.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)C>ClCCl>[C:4]1(=[O:13])[N:5]([CH:6]2[CH2:7][CH2:8][C:9](=[O:12])[CH2:10][CH2:11]2)[C:1](=[O:18])[C:2]2=[CH:17][CH:16]=[CH:15][CH:14]=[C:3]12

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dioneHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 119983912-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindole-1,3-dioneAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-phthalimido cyclohexanol (7.1 g, 0.029 mole) in dichloromethane (250 ml) was treated with pyridinium chlorochromate (8.6 g, 0.04 mole) and the resulting dark mixture was stirred at room temperature overnight. Diethyl ether (50 ml) was added and the mixture filtered through keiselguhr. The filtrate was concentrated in vacuo and the residue purified by column chromatography (SiO2 ; CHCl3 /EtOAc) to give 4-phthalimido cyclohexanone as a white solid (6.4 g).

Aufarbeitung

  1. filtrationthe mixture filtered through keiselguhr
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue purified by column chromatography (SiO2 ; CHCl3 /EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-93286cc698e44aef82cea3e76c3a9196
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464864

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