Reacción #448860

ord-be5871768e79435084d0c7bc4f39b553

Ecuación de reacción

O
water
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
→
C[C@]12C[C@H](F)[C@@H]3c4ccc(O)cc4C[C@@H](CCCCCBr)[C@H]3[C@@H]1CCC2=O
7α-(5-bromopentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one
Rendimiento 73.7%

Reactantes

O
water
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

Reactivos

[Br][Cu][Br]
copper(II) bromide

Disolventes

CC#N
acetonitrile

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónextracted three times with ethyl acetate
  2. 2
    Lavadowashed twice with ammonium chloride, with sodium bicarbonate and common salt
  3. 3
    Otrodried
  4. 4
    Concentraciónconcentrated by evaporation in a vacuum
  5. 5
    OtroAfter the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Procedimiento

17.0 g of copper(II) bromide is added to 27.8 g of 7α-(5-bromopentyl)-11β-fluoro-estr-4-ene-3,17-dione in 190 ml of acetonitrile at 80° C. After 8 hours, the reaction mixture is stirred into water, extracted three times with ethyl acetate, washed twice with ammonium chloride, with sodium bicarbonate and common salt, dried and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient, 20.4 g of 7α-(5-bromopentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained as colorless crystals with a melting point of 178° C.

Fuente

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