Reaktion #459019

ord-381f05b374314aab8b72084c8316d863

Reaktionsgleichung

CCC(=O)O.CCC(=O)O.C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43CO)[C@@H]1CC[C@@H]2O
17β,19-Dihydroxy-4-androsten-3-one dipropionate
N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O
dichlorodicyanobenzoquinone
→
CCC(=O)O.CCC(=O)O.C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43CO)[C@@H]1CC[C@@H]2O
17β,19-dihydroxy-1,4-androstadien-3-one dipropionate

Edukte

CCC(=O)O.CCC(=O)O.C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43CO)[C@@H]1CC[C@@H]2O
17β,19-Dihydroxy-4-androsten-3-one dipropionate
N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O
dichlorodicyanobenzoquinone

Reagenzien

Keine

Lösungsmittel

C1COCCO1
dioxane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe mixture is cooled
  2. 2
    Filtrationfiltered
  3. 3
    Einengenthe filtrate concentrated under vacuum
  4. 4
    workup.ADDITIONMethylenechloride is added
  5. 5
    Filtrationthe resulting mixture filtered
  6. 6
    WaschenThe filtrate is washed well with water
  7. 7
    Trocknendried over sodium sulfate
  8. 8
    Sonstigethe solvent removed
  9. 9
    WaschenChromatography of the residue on silica gel and elution with methylenechloride
  10. 10
    Sonstigeprovides a solid which
  11. 11
    Sonstigeis crystallized from acetone-hexane

Vorschrift

17β,19-Dihydroxy-4-androsten-3-one dipropionate and dichlorodicyanobenzoquinone are refluxed in anhydrous dioxane for a period of 48 hours. The mixture is cooled and filtered and the filtrate concentrated under vacuum. Methylenechloride is added and the resulting mixture filtered. The filtrate is washed well with water, dried over sodium sulfate and the solvent removed. Chromatography of the residue on silica gel and elution with methylenechloride provides a solid which is crystallized from acetone-hexane to yield the desired 17β,19-dihydroxy-1,4-androstadien-3-one dipropionate.

Quelle

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