Reaktion #320688

ord-9cf78d01e58f4db28c84320d4e73d7e1

Reaktionsgleichung

O
water
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(=O)OCC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC=CC[C@]4(C)[C@H]3C(=O)C[C@]12C
(5α)-21-(acetyloxy)pregn-2-ene-11,20-dione
→
C[C@]12CC=CC[C@@H]1CC[C@H]1[C@@H]3CC[C@H](C(=O)CO)[C@@]3(C)CC(=O)[C@@H]12
(5α)-21-hydroxypregn-2-ene-11,20-dione

Edukte

O
water
—
3-ene-isomer
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(=O)OCC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC=CC[C@]4(C)[C@H]3C(=O)C[C@]12C
(5α)-21-(acetyloxy)pregn-2-ene-11,20-dione

Reagenzien

Keine

Lösungsmittel

CO
methanol
CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    ExtraktionThe mixture was extracted with dichloromethane
  2. 2
    Waschenthe organic phase was washed with water
  3. 3
    Trocknendried over sodium sulfate
  4. 4
    Sonstigethe solvent was removed under reduced pressure
  5. 5
    SonstigeThe residue was chromatographed on silica gel

Vorschrift

A solution of potassium carbonate in methanol (190 ml; 0.19M) was added to a suspension of (5α)-21-(acetyloxy)pregn-2-ene-11,20-dione and its 3-ene-isomer (18.8 g) in methanol (188 ml). The resulting solution was stirred at room temperature for 30 min and poured into water (3.7 l). The mixture was extracted with dichloromethane and the organic phase was washed with water, dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel to give a mixture (3:1) (15.3 g) of (5α)-21-hydroxypregn-2-ene-11,20-dione and its 3-ene-isomer.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05593983uspto-grants-1997_01