Reacción #448859

ord-27443af2c42d447d971f64b9399a9bda

Ecuación de reacción

C[C@]12C[C@H](F)[C@H]3[C@@H]([C@H](CCCCCO)CC4=CC(=O)CC[C@@H]43)[C@@H]1CCC2=O
11β-fluoro-7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
BrC(Br)(Br)Br
carbon tetrabromide
→
C[C@]12C[C@H](F)[C@H]3[C@@H]([C@H](CCCCCBr)CC4=CC(=O)CC[C@@H]43)[C@@H]1CCC2=O
7α-(5-bromopentyl)-11β-fluoro-estr-4-ene-3,17-dione
Rendimiento 74.0%

Reactantes

C[C@]12C[C@H](F)[C@H]3[C@@H]([C@H](CCCCCO)CC4=CC(=O)CC[C@@H]43)[C@@H]1CCC2=O
11β-fluoro-7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
BrC(Br)(Br)Br
carbon tetrabromide

Reactivos

Ninguno

Disolventes

ClCCl
dichloromethane
ClCCl
dichloromethane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadowashed with water, saturated sodium bicarbonate and common salt solution
  2. 2
    OtroThe organic phase is dried on sodium sulfate
  3. 3
    Concentraciónconcentrated by evaporation in a vacuum
  4. 4
    OtroThen, the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Procedimiento

A solution of 33 g of 11β-fluoro-7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione in 330 ml of dichloromethane is mixed at -5° C .with 28.9 g of triphenylphosphine and 36.7 g of carbon tetrabromide, and it is stirred for 0.5 hour. Then, dichloromethane is added and washed with water, saturated sodium bicarbonate and common salt solution. The organic phase is dried on sodium sulfate and concentrated by evaporation in a vacuum. Then, the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient. 28.5 g of 7α-(5-bromopentyl)-11β-fluoro-estr-4-ene-3,17-dione with a melting point of 75°-76° C. is obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05866560uspto-grants-1999_02