Reaction #94829

ord-846a8806a8f34412a7df715c710e35fc

Reaction equation

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

Reactants

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

Reagents

None

Solvents

CO
methanol
CCCCCC
hexane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

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.v1Patent: US04342702uspto-grants-1982_08