Reacción #93001

Ecuación de reacción

ethyl acetate

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

N,N-dimethylaniline

cyclopentylacetyl chloride

→

above-identified compound

16β-Ethyl-17β-cyclopentylacetoxyacetoxy-4-estren-3-one

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis added
2. 2
   LavadoThe mixture is washed with 10% H3PO4, water, 10% aqueous NaHCO3, water and saturated aqueous sodium chloride solution in that order
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONThe solvent is then distilled off
5. 5
   Lavadopassage of 80 ml of diisopropyl ether-n-hexane (1:10), elution
6. 6
   workup.ADDITIONis carried out with 80 ml of a 1:1 mixture of the same solvents
7. 7
   OtroThe eluate is evaporated under reduced pressure
8. 8
   Otroto remove the solvent

Procedimiento

In 10 ml of dichloromethane are dissolved 0.5 g of 16β-ethyl-17β-glycoloyloxy-4-estren-3-one and 0.2 ml of N,N-dimethylaniline and, with stirring, 0.3 ml of cyclopentylacetyl chloride is added. The mixture is stirred at room temperature (15°-25° C.) overnight and 150 ml of ethyl acetate is added. The mixture is washed with 10% H3PO4, water, 10% aqueous NaHCO3, water and saturated aqueous sodium chloride solution in that order and dried over anhydrous magnesium sulfate. The solvent is then distilled off and the residue is subjected to column chromatography. Following passage of 80 ml of diisopropyl ether-n-hexane (1:10), elution is carried out with 80 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.1 g of the above-identified compound as a colorless viscous oil.

Fuente