Reaktion #95329

ord-20e6132d08ec404db949486005c258bd

Reaktionsgleichung

C[C@H]1CC2(C[C@@H]3CC[C@H]4[C@@H]5CC[C@H](O)[C@@]5(C)CC[C@@H]4[C@]31C)OCCO2
3,3-ethylenedioxy-1α-methyl-5α-androstan-17β-ol
[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
pyridinium chlorochromate
CC(=O)[O-].[Na+]
sodium acetate
→
CC1CC2(C[C@@H]3CC[C@@H]4[C@H](CC[C@]5(C)C(=O)CC[C@@H]45)[C@@]13C)OCCO2
3,3-ethylenedioxy-1-methyl-5α-androstan-17-one
Ausbeute 94.0%

Edukte

C[C@H]1CC2(C[C@@H]3CC[C@H]4[C@@H]5CC[C@H](O)[C@@]5(C)CC[C@@H]4[C@]31C)OCCO2
3,3-ethylenedioxy-1α-methyl-5α-androstan-17β-ol
[O]=[Cr](=[O])([O-])[Cl].c1cc[nH+]cc1
pyridinium chlorochromate
CC(=O)[O-].[Na+]
sodium acetate

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane
CCOCC
ether

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfiltered off from the insoluble proportions
  2. 2
    Waschenthe filtrate is washed with water
  3. 3
    SonstigeAfter drying
  4. 4
    Sonstigeevaporation

Vorschrift

23 g of 3,3-ethylenedioxy-1α-methyl-5α-androstan-17β-ol is agitated for 1 hour at room temperature in 230 ml of dichloromethane with 20 g of pyridinium chlorochromate in the presence of 20 g of sodium acetate. The reaction solution is then diluted with ether, filtered off from the insoluble proportions, and the filtrate is washed with water. After drying and evaporation, 21.5 g of 3,3-ethylenedioxy-1-methyl-5α-androstan-17-one is obtained as the crude product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04344941uspto-grants-1982_08