Reaktion #1243234

ord-86a6f5e699714ab788aa129b4ee7f097

Reaktionsgleichung

CCC[C@@H]1C[C@H]2[C@@H]3CCC4=C(CCC(=O)C4)C3=CC[C@]2(C)[C@H]1OC(C)=O
17β-acetoxy-16α-propyl-5(10),9(11)-estradien-3-one
N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O
dichlorodicyano-p-benzoquinone
→
CCC[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CCC4=C3C=C[C@]2(C)[C@H]1OC(C)=O
17β-acetoxy-16α-propyl-4,9,11-estratrien-3-one
Ausbeute 93.9%

Edukte

CCC[C@@H]1C[C@H]2[C@@H]3CCC4=C(CCC(=O)C4)C3=CC[C@]2(C)[C@H]1OC(C)=O
17β-acetoxy-16α-propyl-5(10),9(11)-estradien-3-one
N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O
dichlorodicyano-p-benzoquinone

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter crystallization from diisopropyl ether

Vorschrift

A solution of 1.5 g of 17β-acetoxy-16α-propyl-5(10),9(11)-estradien-3-one in 100 ml of methylene chloride is dehydrogenated with 1.8 g of dichlorodicyano-p-benzoquinone under the conditions of Example 1. After crystallization from diisopropyl ether, 1.4 g of 17β-acetoxy-16α-propyl-4,9,11-estratrien-3-one is obtained, m.p. 108°-109° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04333928uspto-grants-1982_06