Reaktion #78035

ord-456245f79c4a471597f8d42a17d413f7

Reaktionsgleichung

C[C@]12CCC(=O)C3OC31CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)C[C@@H]3C[C@]312
17β-hydroxy-4,5-epoxy-14α,15α-methylene-androstan-3-one
Cl
hydrochloric acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
→
C[C@]12CCC(=O)C(Cl)=C1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)C[C@@H]3C[C@]312
4-chloro-17β-hydroxy-14α,15α-methylene-androst-4-ene-3-one

Edukte

C[C@]12CCC(=O)C3OC31CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)C[C@@H]3C[C@]312
17β-hydroxy-4,5-epoxy-14α,15α-methylene-androstan-3-one
Cl
hydrochloric acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe acetone is evaporated
  2. 2
    ExtraktionThe residue is extracted with dichloromethane
  3. 3
    SonstigeThe organic extracts are dried
  4. 4
    Einengenconcentrated
  5. 5
    SonstigeAfter crystallization from ethanol

Vorschrift

17β-hydroxy-4,5-epoxy-14α,15α-methylene-androstan-3-one (1.5 g) is dissolved in 150 mL of acetone and treated at 0° C. with 5.5 mL of concentrated hydrochloric acid. After 24 hours at 0° C., the reaction mixture is neutralized with sodium carbonate solution and the acetone is evaporated. The residue is extracted with dichloromethane. The organic extracts are dried and concentrated. After crystallization from ethanol, 4-chloro-17β-hydroxy-14α,15α-methylene-androst-4-ene-3-one is obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06710039B1uspto-grants-2004_03