Reacción #92991

Ecuación de reacción

16β-ethyl-17β-bromoacetoxy-4-estren-3-one

n-octanoic acid

→

above-identified compound

16β-Ethyl-17β-n-octanoyloxyacetoxy-4-estren-3-one

Disolventes

acetone

NaOH

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONare serially added to the above solution
2. 2
   TemperaturaThe mixture is refluxed for 4 hours
3. 3
   workup.DISTILLATIONThe solvent is distilled off under reduced pressure
4. 4
   Extracciónthe residue is extracted with 150 ml of ethyl acetate
5. 5
   OtroThe organic layer is separated
6. 6
   Lavadowashed with water and saturated aqueous sodium chloride solution
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
9. 9
   Lavadopassage of 50 ml of diisopropyl ether, elution
10. 10
    OtroThe eluate is evaporated under reduced pressure
11. 11
    Otroto remove the solvent

Procedimiento

In 60 ml of acetone is dissolved 1.0 ml of n-octanoic acid, and 3.0 ml of 2N-NaOH, 15 ml of water and 1.8 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one are serially added to the above solution. The mixture is refluxed for 4 hours. The solvent is distilled off under reduced pressure and the residue is extracted with 150 ml of ethyl acetate. The organic layer is separated, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 50 ml of diisopropyl ether, elution is carried out with 300 ml of the same solvent. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.7 g of the above-identified compound as a colorless oil.

Fuente