Reaktion #93012

Reaktionsgleichung

16β-ethyl-17β-hydroxy-4,9(10)-estradien-3-one

n-hexanoyloxyacetyl chloride

ethyl acetate

sodium hydrogen carbonate

→

above-identified compound

16β-Ethyl-17β-n-hexanoyloxyacetoxy-4,9(10)-estradien-3-one

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added
2. 2
   SonstigeThe organic layer is separated
3. 3
   Extraktionthe aqueous layer is extracted with ethyl acetate
4. 4
   Waschenwashed with water and saturated aqueous sodium chloride solution
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
7. 7
   Sonstigethe residue is chromatographed on a silica gel column
8. 8
   Waschenpassage of diisopropyl ether-n-hexane (1:1), elution
9. 9
   workup.ADDITIONis carried out with 1000 ml of a 3:2 mixture of the same solvents
10. 10
    SonstigeThe eluate is evaporated under reduced pressure
11. 11
    Sonstigeto remove the solvent

Vorschrift

In 20 ml of toluene are dissolved 1.5 g of 16β-ethyl-17β-hydroxy-4,9(10)-estradien-3-one and 1.92 g of 4-dimethylaminopyridine, and 1.6 ml of n-hexanoyloxyacetyl chloride is added. The mixture is stirred at 50°-60° C. for 3 hours. After cooling to 25° C., the mixture is poured into a mixture of ethyl acetate (200 ml) and saturated aqueous sodium hydrogen carbonate (50 ml). The organic layer is separated and the aqueous layer is extracted with ethyl acetate. These organic layers are combined, 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 chromatographed on a silica gel column. Following passage of diisopropyl ether-n-hexane (1:1), elution is carried out with 1000 ml of a 3:2 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.69 g of the above-identified compound as a light-yellow viscous oil.

Quelle