Reaktion #926928

ord-79e24b75c33b4811ac7668a8a3e76a5d

Reaktionsgleichung

COc1cc2c(c(OC(C)=O)c1)[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC2
1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one
→
COc1cc2c(c(OC(C)=O)c1)[C@H]1CC[C@]3(C)[C@@H](O)CC[C@H]3[C@@H]1CC2
1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17β-ol

Edukte

COc1cc2c(c(OC(C)=O)c1)[C@H]1CC[C@]3(C)C(=O)CC[C@H]3[C@@H]1CC2
1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one

Reagenzien

[O]=[Pt]=[O]
PtO2

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationAfter filtration and evaporation of the solvent in vacuo
  2. 2
    Sonstigethe oily residue is chromatographed on 250 g of neutral silica gel
  3. 3
    Wascheninitially eluting with benzene
  4. 4
    SonstigeEvaporation of the solvent in vacuo
  5. 5
    Sonstigefollowed by recrystallization from ether

Vorschrift

A solution of 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17-one (4.9 g, 14.3 mM) in 250 ml of ethanol is shaken with PtO2 (1 g) under N2 at 40 psi for 7 hrs. After filtration and evaporation of the solvent in vacuo, the oily residue is chromatographed on 250 g of neutral silica gel, initially eluting with benzene and finally progressing to 5% ethyl acetate:benzene. Evaporation of the solvent in vacuo, followed by recrystallization from ether:hexane gives 1-acetoxy-3-methoxyestra-1,3,5(10)-trien-17β-ol, yield 2.35 g (48%), m.p. 107°-110° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04096253uspto-grants-1978_06