Reaktion #1243231

ord-0a798ff6753a4d44856a5f2ac89f70fe

Reaktionsgleichung

N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O
dichlorodicyano-p-benzoquinone
CC[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-ethyl-5(10),9(11)-estradien-3-one
→
CC[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-ethyl-4,9,11-estratrien-3-one
Ausbeute 88.0%

Edukte

N#CC1=C(C#N)C(=O)C(Cl)=C(Cl)C1=O
dichlorodicyano-p-benzoquinone
CC[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-ethyl-5(10),9(11)-estradien-3-one

Reagenzien

Keine

Lösungsmittel

Cc1ccccc1
toluene
ClCCl
methylene chloride
Cc1ccccc1
toluene
ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationfiltered over neutral aluminum oxide
  2. 2
    Einengenconcentrated
  3. 3
    SonstigeAfter crystallization from diethyl ether

Vorschrift

3.2 g of 17β-acetoxy-16α-ethyl-5(10),9(11)-estradien-3-one is dissolved in 120 ml of toluene and 40 ml of methylene chloride and combined at room temperature dropwise with a solution of 5.5 g of dichlorodicyano-p-benzoquinone in 80 ml of toluene and 20 ml of methylene chloride. The mixture is stirred for 16 hours at room temperature, filtered over neutral aluminum oxide, and concentrated. After crystallization from diethyl ether, 2.8 g of 17β-acetoxy-16α-ethyl-4,9,11-estratrien-3-one is obtained, m.p. 95°-98° C.

Quelle

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