Reaktion #2485157

ord-2fa7a460882c4a3f94cde76f0db349b7

Reaktionsgleichung

C[C@H]1CCC=C2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@]21CO
1α-Methyl-4-androstene-17β,19-diol
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones Reagent
O=S([O-])[O-].[Na+].[Na+]
sodium sulfite
→
C[C@H]1CCC=C2CC[C@@H]3[C@H](CC[C@]4(C)C(=O)CC[C@@H]34)[C@]21C=O
1α-methyl-4-androstene-17,19-dione

Edukte

C[C@H]1CCC=C2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@]21CO
1α-Methyl-4-androstene-17β,19-diol
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones Reagent
O=S([O-])[O-].[Na+].[Na+]
sodium sulfite

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Temperatur
40°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturcooled
  2. 2
    FiltrationAfter several hours the crystals which form are collected by filtration
  3. 3
    Waschenthoroughly washed with water and air
  4. 4
    Sonstigedried
  5. 5
    SonstigeCrystallization from hexane

Vorschrift

1α-Methyl-4-androstene-17β,19-diol is dissolved in dimethylformamide at 40° C. and two equivalents of Jones Reagent are added all at once. The mixture is stirred for about 5 hours at 40° C., cooled and a 1% aqueous sodium sulfite solution is added. After several hours the crystals which form are collected by filtration, thoroughly washed with water and air dried. Crystallization from hexane yields the desired 1α-methyl-4-androstene-17,19-dione.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04022769uspto-grants-1977_05