Reacción #92988

Ecuación de reacción

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

sodium n-hexanoate

→

above-identified compound

Rendimiento 77.5%

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

Rendimiento 77.5%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe solution is refluxed for 6 hours
2. 2
   workup.DISTILLATIONThe solvent is distilled off under reduced pressure
3. 3
   Extracciónthe residue is extracted with 300 ml of ethyl acetate
4. 4
   OtroThe organic layer is separated
5. 5
   Lavadowashed with water and saturated aqueous sodium chloride solution
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
8. 8
   Lavadopassage of 750 ml of diisopropyl ether-n-hexane (9:1), elution
9. 9
   workup.ADDITIONis carried out with 1000 ml of a 1:1 mixture of the same solvents
10. 10
    OtroThe eluate is evaporated under reduced pressure
11. 11
    Otroto remove the solvent

Procedimiento

In 150 ml of 50% aqueous acetone are dissolved 5.0 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 2.5 g of sodium n-hexanoate and the solution is refluxed for 6 hours. The solvent is distilled off under reduced pressure and the residue is extracted with 300 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 750 ml of diisopropyl ether-n-hexane (9:1), elution is carried out with 1000 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 4.2 g of the above-identified compound as a light-yellow viscous oil.

Fuente