Reaktion #94829

ord-846a8806a8f34412a7df715c710e35fc

Reaktionsgleichung

Cl
hydrochloric acid
COC(=CCl)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@@]21C
21-Chloro-17α-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one
C1CCOC1
THF
CC(C)=O
acetone
→
C[C@]12CCC(=O)C=C1CC[C@@H]1C2=CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CCl
title compound
C[C@]12CCC(=O)C=C1CC[C@@H]1C2=CC[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CCl
21-Chloro-17α-hydroxypregna-4,9(11)-diene-3,20-dione

Edukte

Cl
hydrochloric acid
COC(=CCl)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@@]21C
21-Chloro-17α-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one
C1CCOC1
THF
CC(C)=O
acetone

Reagenzien

Keine

Lösungsmittel

CO
methanol
CCCCCC
hexane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe resulting slurry heated at 40° for 1.5 hours
  2. 2
    TemperaturThe mixture is cooled to 20°-25°
  3. 3
    SonstigeThe solids are isolated by filtration
  4. 4
    Waschenwashed with hexane/ethyl acetate (85/15, 13 ml)

Vorschrift

21-Chloro-17α-hydroxy-20-methoxypregna-4,9(11),20-trien-3-one (VII, Example 4, 1.0 g), THF (4 ml), acetone (4.9 ml), and methanol (1.4 ml) are mixed. Aqueous hydrochloric acid (6 N, 0.44 ml) is added and the resulting slurry heated at 40° for 1.5 hours. The mixture is cooled to 20°-25° and diluted with hexane (3 ml). The solids are isolated by filtration and washed with hexane/ethyl acetate (85/15, 13 ml) to give the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04342702uspto-grants-1982_08