Reaktion #1477965

ord-2e57862597534487b42c416011717cc4

Reaktionsgleichung

C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43CO)[C@@H]1CCC2=O
3β,19-dihydroxy-5-androsten-17-one
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones Reagent
→
C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@@]43C=O)[C@@H]1CCC2=O
5-androstene-3,17,19-trione

Edukte

C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@@]43CO)[C@@H]1CCC2=O
3β,19-dihydroxy-5-androsten-17-one
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
    SonstigeAfter an additional 15 minutes the upper acetone layer is decanted
  2. 2
    workup.ADDITIONpoured onto ice water
  3. 3
    FiltrationThe precipitate which forms is filtered
  4. 4
    Waschenwashed with water
  5. 5
    workup.DISSOLUTIONdissolved in ether
  6. 6
    TrocknenThe ether solution is dried over magnesium sulfate
  7. 7
    Einengenconcentrated under reduced pressure
  8. 8
    SonstigeCrystallization of the residue from an acetone-hexane solution

Vorschrift

To a solution of 3β,19-dihydroxy-5-androsten-17-one in acetone at 10° C. is added two equivalents of Jones Reagent with stirring. After an additional 15 minutes the upper acetone layer is decanted and poured onto ice water. The precipitate which forms is filtered, washed with water and dissolved in ether. The ether solution is dried over magnesium sulfate and concentrated under reduced pressure. Crystallization of the residue from an acetone-hexane solution yields 5-androstene-3,17,19-trione.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04139617uspto-grants-1979_02