Reacción #92984

Ecuación de reacción

ethyl acetate

16β-ethyl-17β-hydroxy-4-estren-3-one

dimethylaniline

2-bromo-2-methylpropionyl bromide

→

above-identified compound

16β-Ethyl-17β-(2-bromo-2-methylpropionyloxy)4-estren-3-one

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis added to the above solution
2. 2
   LavadoThe mixture is washed with 10% phosphoric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in that order
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
5. 5
   Lavadopassage of 400 ml of diisopropyl ether-n-hexane (1:1), elution
6. 6
   OtroThe eluate is evaporated under reduced pressure
7. 7
   Otroto remove the solvent

Procedimiento

In 30 ml of dichloromethane are dissolved 3.2 g of 16β-ethyl-17β-hydroxy-4-estren-3-one and 1.2 ml of dimethylaniline and, with stirring at room temperature (15°-25° C.), 1.0 ml of 2-bromo-2-methylpropionyl bromide is added to the above solution. The mixture is stirred at room temperature (15°-25° C.) for 16 hours, followed by addition of 300 ml of ethyl acetate. The mixture is washed with 10% phosphoric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride in that order 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 400 ml of diisopropyl ether-n-hexane (1:1), elution is carried out with 800 ml of the same solvent system. The eluate is evaporated under reduced pressure to remove the solvent, giving 2.6 g of the above-identified compound as a light-yellow viscous oil.

Fuente