Reacción #78035

ord-456245f79c4a471597f8d42a17d413f7

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

CC(C)=O
acetone

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothe acetone is evaporated
  2. 2
    ExtracciónThe residue is extracted with dichloromethane
  3. 3
    OtroThe organic extracts are dried
  4. 4
    Concentraciónconcentrated
  5. 5
    OtroAfter crystallization from ethanol

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US06710039B1uspto-grants-2004_03