Hydroquinone → 6-Methyl-5-(3-methylisoxazol-5-yl)-7,7-dimethoxy-1,2,3,4-tetrachlorobicyclo[2.2.1]hept-2-ene

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Reaktionsgleichung

[CH3:1][O:2][C:3]1([O:12][CH3:13])[C:7]([Cl:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]1[Cl:11].C(=O)([O-])O.[Na+].[CH3:19][C:20]1[CH:24]=[C:23](/[CH:25]=[CH:26]/[CH3:27])[O:22][N:21]=1.C1(C=CC(O)=CC=1)O>C(OCC)(=O)C>[CH3:27][CH:26]1[C:4]2([Cl:11])[C:3]([O:2][CH3:1])([O:12][CH3:13])[C:7]([Cl:8])([C:6]([Cl:9])=[C:5]2[Cl:10])[CH:25]1[C:23]1[O:22][N:21]=[C:20]([CH3:19])[CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 180 °C

Versuchsvorschrift

1.07 g of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopenta-1,3-diene, 0.34 g of sodium hydrogen carbonate, 0.50g of trans-1-(3-methylisoxazol-5-yl)-1-propene and 0.05 g of hydroquinone were mixed and heated with stirring at 180° C. for 7 hours. The reaction solution was cooled and ethyl acetate was added. Insoluble matter was removed by filtration. Then the solvent was concentrated under reduced pressure. The obtained crude product was purified on silica gel column chromatography (elution with benzene) to give 0.70 g of the title compound as a mixture of isomers.

Aufarbeitung

temperatureheated
temperatureThe reaction solution was cooled
customInsoluble matter was removed by filtration
concentrationThen the solvent was concentrated under reduced pressure
customThe obtained crude product
customwas purified on silica gel column chromatography (elution with benzene)

Quellen und Nachweise

ORD-Eintrag: ord-5501bf9ea2dd4b519af242077d9fb38e
Quelldatensatz: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06756497B1

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