Reaktion #93001

Reaktionsgleichung

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

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added
2. 2
   WaschenThe mixture is washed with 10% H3PO4, water, 10% aqueous NaHCO3, water and saturated aqueous sodium chloride solution in that order
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONThe solvent is then distilled off
5. 5
   Waschenpassage 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
   SonstigeThe eluate is evaporated under reduced pressure
8. 8
   Sonstigeto remove the solvent

Vorschrift

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.

Quelle