Reaktion #94827

ord-dcbf84c204bc48bd8afb3fc0c8d16176

Reaktionsgleichung

C[C@]12CCC(=O)C=C1CC[C@@H]1C2=CC[C@]2(C)C(=C=C(Cl)S(=O)c3ccccc3)CC[C@@H]12
21-Chloro-21-(phenylsulfinyl)pregna-4,9(11),17(20),20-tetraen-3-one
C1CCOC1
THF
C[O-].[Na+]
Sodium methoxide
→
COC(=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@]12C)C(Cl)S(=O)c1ccccc1
title compound
COC(=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)C3=CC[C@]12C)C(Cl)S(=O)c1ccccc1
21-Chloro-20-methoxy-21-(phenylsulfinyl)pregna-4,9(11),17(20)-trien-3-one

Edukte

C[C@]12CCC(=O)C=C1CC[C@@H]1C2=CC[C@]2(C)C(=C=C(Cl)S(=O)c3ccccc3)CC[C@@H]12
21-Chloro-21-(phenylsulfinyl)pregna-4,9(11),17(20),20-tetraen-3-one
C1CCOC1
THF
C[O-].[Na+]
Sodium methoxide

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturcooled to 0°-5° under nitrogen
  2. 2
    workup.STIRRINGThe mixture is stirred 1 hr
  3. 3
    Sonstigequenched with water (10 ml)
  4. 4
    ExtraktionThe mixture is extracted with ethyl acetate (2×15 ml)
  5. 5
    Trocknendried over sodium sulfate
  6. 6
    Einengenconcentrated under reduced pressure

Vorschrift

21-Chloro-21-(phenylsulfinyl)pregna-4,9(11),17(20),20-tetraen-3-one, (V, Example 2, 100 mg) and THF (1 ml) are slurried and cooled to 0°-5° under nitrogen. Sodium methoxide in methanol (25%, 0.05 ml) is added with stirring. The mixture is stirred 1 hr and then quenched with water (10 ml). The mixture is extracted with ethyl acetate (2×15 ml). The organic extracts are combined, backwashed with water (10 ml), dried over sodium sulfate and concentrated under reduced pressure to give the title compound.

Quelle

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