Reaktion #459592

ord-fa761554a1524ab9a6abff25e2af2332

Reaktionsgleichung

CSC1(SC)CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
9-fluoro-11β-hydroxy-17,17-bis-(methylthio)androsta-1,4-diene-3-one
→
CSC1=CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C
title compound
Ausbeute 91.7%
CSC1=CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]12C
9-Fluoro-11β-hydroxy-17-(methylthio)androsta-1,4,16-trien-3-one
Ausbeute 91.7%

Edukte

CSC1(SC)CC[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
9-fluoro-11β-hydroxy-17,17-bis-(methylthio)androsta-1,4-diene-3-one

Reagenzien

Keine

Lösungsmittel

CCc1ccccc1CC
diethylbenzene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.DISTILLATIONis slowly distilled from a bath at 220° C
  2. 2
    workup.WAITIn a few minutes
  3. 3
    Sonstigea clear solution results
  4. 4
    TemperaturOn cooling in an ice bath

Vorschrift

A suspension of 9-fluoro-11β-hydroxy-17,17-bis-(methylthio)androsta-1,4-diene-3-one (3.6 g) in diethylbenzene (250 ml) is slowly distilled from a bath at 220° C. In a few minutes, a clear solution results and the starting material disappears. On cooling in an ice bath, the solution deposits small needles of the analytical specimen of the title compound, (2.9 g), melting point 268° C (dec.). (discoloration starts at 263° C).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04091036uspto-grants-1978_05