Reaktion #459028

ord-418bc839e03d4f55af1df74410c7c3b8

Reaktionsgleichung

C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)[C@H]5C[C@H]5[C@@]43C)[C@@H]1CC[C@@H]2O
1β,2β-methylene-5-androstene-3β,17β-diol
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent
→
C[C@@]12C(=CC(=O)[C@H]3C[C@H]31)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
1β,2β-methylene-4-androstene-3,17-dione

Edukte

C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)[C@H]5C[C@H]5[C@@]43C)[C@@H]1CC[C@@H]2O
1β,2β-methylene-5-androstene-3β,17β-diol
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONis poured onto ice-water
  2. 2
    Filtrationthe precipitate is collected by filtration
  3. 3
    workup.DISSOLUTIONThe precipitate is dissolved in a solution of sodium methoxide in methanol
  4. 4
    workup.STIRRINGstirred for a period of 30 minutes at room temperature
  5. 5
    SonstigeThe methanol is removed
  6. 6
    Sonstigethe residue triturated with water
  7. 7
    SonstigeThe solid which results
  8. 8
    Filtrationis filtered
  9. 9
    Sonstigecrystallized from acetone

Vorschrift

The 1β,2β-methylene-5-androstene-3β,17β-diol is dissolved in acetone and Jones reagent added until a persistent yellow-orange color appears. After stirring at room temperature for ten minutes the mixture is poured onto ice-water and the precipitate is collected by filtration. The precipitate is dissolved in a solution of sodium methoxide in methanol and stirred for a period of 30 minutes at room temperature. The methanol is removed and the residue triturated with water. The solid which results is filtered and crystallized from acetone to yield 1β,2β-methylene-4-androstene-3,17-dione.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04087524uspto-grants-1978_05