Réaction #94829

ord-846a8806a8f34412a7df715c710e35fc

Équation de réaction

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

Réactifs

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

Réactifs

Aucun

Solvants

CO
methanol
CCCCCC
hexane

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04342702uspto-grants-1982_08