Reaction #92988

Reaction equation

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

sodium n-hexanoate

→

above-identified compound

Yield 77.5%

16β-Ethyl-17β-n-hexanoyloxyacetoxy-4-estren-3-one

Yield 77.5%

Solvents

acetone

Conditions

Workup

1. 1
   Temperaturethe solution is refluxed for 6 hours
2. 2
   workup.DISTILLATIONThe solvent is distilled off under reduced pressure
3. 3
   Extractionthe residue is extracted with 300 ml of ethyl acetate
4. 4
   OtherThe organic layer is separated
5. 5
   Washwashed with water and saturated aqueous sodium chloride solution
6. 6
   Dryingdried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
8. 8
   Washpassage of 750 ml of diisopropyl ether-n-hexane (9:1), elution
9. 9
   workup.ADDITIONis carried out with 1000 ml of a 1:1 mixture of the same solvents
10. 10
    OtherThe eluate is evaporated under reduced pressure
11. 11
    Otherto remove the solvent

Procedure

In 150 ml of 50% aqueous acetone are dissolved 5.0 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 2.5 g of sodium n-hexanoate and the solution is refluxed for 6 hours. The solvent is distilled off under reduced pressure and the residue is extracted with 300 ml of ethyl acetate. The organic layer is separated, 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 subjected to column chromatography. Following passage of 750 ml of diisopropyl ether-n-hexane (9:1), elution is carried out with 1000 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 4.2 g of the above-identified compound as a light-yellow viscous oil.

Source