Illudin M → Dehydroilludin M

HRID 1756112Notes

Reaction equation

HRID 1756112 reaction equation
[CH3:1][C:2]1[C:11]2([CH2:13][CH2:12]2)[C@:10]([OH:15])([CH3:14])[C:8](=[O:9])[C:7]2[C:3]=1[C@@H:4]([OH:18])[C:5]([CH3:17])([CH3:16])[CH:6]=2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[CH3:1][C:2]1[C:11]2([CH2:12][CH2:13]2)[C@:10]([OH:15])([CH3:14])[C:8](=[O:9])[C:7]2=[CH:6][C:5]([CH3:16])([CH3:17])[C:4](=[O:18])[C:3]=12

Participants

5

Reactant 2

HCID 344199Illudin MHCID 2724130Cornforth reagent

Product 1

HCID 362430Dehydroilludin M

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. customequipped with a rubber septum so that an atmosphere of argon
  2. temperaturecould be maintained
  3. filtrationfiltered through a short column of silica gel
  4. washThe column was further eluted with more diethyl ether
  5. concentrationthe combined filtrate was concentrated
  6. customgiving a residue which
  7. customwas chromatographed on silica gel with hexane-ethyl acetate (10:1) as eluent

Sources & evidence

ORD record
ord-6b5d5519b29d4e738fef561b213f73b5
Source dataset
uspto-grants-1995_08
Patent number
US05439936

Reaction notes

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