1,3-Cyclohexadiene → 3a-(3,4-difluorophenyl)-3a,4,7,7a-tetrahydro-2-methyl-4,7-ethano-1H-isoindole-1,3(2H)-dione

HRID 371136

Reaktionsgleichung

Reaktionsgleichung von HRID 371136
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:16])[N:11]([CH3:15])[C:12](=[O:14])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH:17]1[CH2:22][CH2:21][CH:20]=[CH:19][CH:18]=1>C(Cl)(Cl)Cl.C(OCC)(=O)C.CCCCCC>[F:1][C:2]1[CH:3]=[C:4]([C:9]23[CH:19]4[CH2:20][CH2:21][CH:22]([CH:17]=[CH:18]4)[CH:13]2[C:12](=[O:14])[N:11]([CH3:15])[C:10]3=[O:16])[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

6

Edukt 2

HCID 116051,3-CyclohexadieneHCID 135195703-(3,4-difluorophenyl)-1-methyl-1H-pyrrole-2,5-dione

Produkt 1

HCID 135195643a-(3,4-difluorophenyl)-3a,4,7,7a-tetrahydro-2-methyl-4,7-ethano-1H-isoindole-1,3(2H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6212ChloroformLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A 5.0 g amount of 3-(3,4-difluorophenyl)-1-methyl-1H-pyrrole-2,5-dione was dissolved in 25 ml of chloroform with warming. The solution was cooled to room temperature and 2.0 g of cyclohexadiene was added. After prolonged standing another 11/2 ml of diene was added with a small amount of butylated hydroxytoluene. The solution was heated at reflux for 24 hours. The reaction mixture was subjected to high pressure liquid chromatography using a silica gel column and 20% ethyl acetate in hexane as eluent giving 4.9 g of 3a-(3,4-difluorophenyl)-3a,4,7,7a-tetrahydro-2-methyl-4,7-ethano-1H-isoindole-1,3(2H)-dione as a white solid, mp 125°-127° C.

Aufarbeitung

  1. temperaturewith warming
  2. temperatureThe solution was heated
  3. temperatureat reflux for 24 hours

Quellen und Nachweise

ORD-Eintrag
ord-28eebc703d3b42c4b0d28ce79db8d281
Quelldatensatz
uspto-grants-1985_07
Patentnummer
US04529736

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