Reaktion #7508

ord-faa2f348d6f5478eb5c5bd468fd5e72f

Reaktionsgleichung

OCCO
ethylene glycol
Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1
pyridinium p-toluenesulfonate
CCCCCC.CCOC(C)=O
EtOAc Hexane
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O
Compound 4
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O
3-hydroxy-5βestran-17-one
→
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC21OCCO1
title compound
Ausbeute 94.8%
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC21OCCO1
3-hydroxy-5β-estran-17-one ethylene ketal
Ausbeute 94.8%

Edukte

OCCO
ethylene glycol
Cc1ccc(S(=O)(=O)[O-])cc1.c1cc[nH+]cc1
pyridinium p-toluenesulfonate
CCCCCC.CCOC(C)=O
EtOAc Hexane
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O
Compound 4
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(O)CC[C@@H]43)[C@@H]1CCC2=O
3-hydroxy-5βestran-17-one

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
EtOAc
c1ccccc1
benzene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturrefluxed
  2. 2
    Waschenwashed twice with brine
  3. 3
    Sonstigedried on Na2SO4
  4. 4
    Sonstigethe solvents removed under reduced pressure

Vorschrift

Compound 4(10 g, 36.2 mmol) was dissolved in dry benzene (150 ml) mixed with ethylene glycol (25 ml, 280 mmol) and pyridinium p-toluenesulfonate (1 g, 3.9 mmol) and refluxed using a Dean-stark separator overnight till no starting material was detected by TLC. The cold solution was diluted with EtOAc (100 ml), washed twice with brine, dried on Na2SO4 and the solvents removed under reduced pressure. Flash-chromatography on silica gel with EtOAc: Hexane 4:6 as eluant to give 11.0 g (94.5% yield) the title compound as a white solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07087590B2uspto-grants-2006_08