Reacción #94829

ord-846a8806a8f34412a7df715c710e35fc

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

CO
methanol
CCCCCC
hexane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04342702uspto-grants-1982_08