Reaktion #347154

Reaktionsgleichung

illudin M

pyridinium dichromate

→

desired compound

Dehydroilludin M

Lösungsmittel

diethyl ether

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a rubber septum so that an atmosphere of argon
2. 2
   Temperaturcould be maintained
3. 3
   Filtrationfiltered through a short column of silica gel
4. 4
   WaschenThe column was further eluted with more diethyl ether
5. 5
   Einengenthe combined filtrate was concentrated
6. 6
   Sonstigegiving a residue which
7. 7
   Sonstigewas chromatographed on silica gel with hexane-ethyl acetate (10:1) as eluent

Vorschrift

A mixture of illudin M (200 mg) and pyridinium dichromate (1 g) in dry dichloromethane (60 ml) was stirred at room temperature in a flask equipped with a rubber septum so that an atmosphere of argon could be maintained. After 20 hours, the reaction mixture was diluted with diethyl ether (20 ml) and filtered through a short column of silica gel. The column was further eluted with more diethyl ether and the combined filtrate was concentrated, giving a residue which was chromatographed on silica gel with hexane-ethyl acetate (10:1) as eluent. The desired compound was obtained in early fractions from the chromatography. The yield was 140 mg of white crystals melting at 64°-65° C. NMR spectral data were recorded for this compound.

Quelle