Reacción #92990

Ecuación de reacción

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

2-ethylbutyric acid

→

above-identified compound

16β-Ethyl-17β-(2-ethylbutyryl)oxyacetoxy-4-estren-3-one

Disolventes

acetone

NaOH

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture is refluxed for 3 hours
2. 2
   workup.DISTILLATIONThe acetone is distilled off under reduced pressure
3. 3
   Extracciónthe residue is extracted with two 100 ml portions of ethyl acetate
4. 4
   Lavadowashed with water and saturated aqueous sodium chloride
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
7. 7
   Lavadopassage of 50 ml of ether, elution
8. 8
   OtroThe eluate is evaporated under reduced pressure
9. 9
   Otroto remove the solvent

Procedimiento

In 35 ml of acetone is dissolved 1.0 ml of 2-ethylbutyric acid, and 4.6 ml of 2N-NaOH and then 1.9 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one are added to the above solution. The mixture is refluxed for 3 hours. The acetone is distilled off under reduced pressure and the residue is extracted with two 100 ml portions of ethyl acetate. The organic layers are combined, washed with water and saturated aqueous sodium chloride 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 ether, elution is carried out with 300 ml of the same solvent. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.63 g of the above-identified compound as a light-yellow viscous oil.

Fuente