Reaktion #1060275

ord-8f54adf58e09490dbfec06707d1f4d48

Reaktionsgleichung

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43CO)[C@@H]1CCC2=O
19-hydroxyandrost-4-ene-3,17-dione
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent
→
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C=O)[C@@H]1CCC2=O
3,17-dioxoandrost-4en-19-al

Edukte

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43CO)[C@@H]1CCC2=O
19-hydroxyandrost-4-ene-3,17-dione
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
    Filtrationfiltered
  2. 2
    Sonstigethe solvent removed under reduced pressure at 35° C
  3. 3
    SonstigeThe ether layer is collected
  4. 4
    Trocknendried over magnesium sulfate
  5. 5
    Filtrationfiltered
  6. 6
    Sonstigethe solvent removed
  7. 7
    SonstigeThe residue is crystallized from acetone-hexane

Vorschrift

To a solution of 30 g. of 19-hydroxyandrost-4-ene-3,17-dione in 3 liters of acetone cooled in an ice bath is added 28 ml of Jones reagent over a one hour period. The reaction mixture is stirred for an additional fifteen minutes, filtered and the solvent removed under reduced pressure at 35° C. The residue is taken up in a large volume of ether and 1.5 liters of water. The ether layer is collected, dried over magnesium sulfate, filtered and the solvent removed. The residue is crystallized from acetone-hexane to give 3,17-dioxoandrost-4en-19-al, M.P. 126°-129° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04054651uspto-grants-1977_10