Reacción #93005

Ecuación de reacción

n-heptanoic acid

NaOH

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

DMF

→

above-identified compound

Rendimiento 64.0%

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

Rendimiento 64.0%

Disolventes

acetone

water

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONare serially added to the above solution
2. 2
   TemperaturaThe mixture is refluxed for 5 hours
3. 3
   TemperaturaAfter cooling
4. 4
   Lavadothe mixture is washed with water and saturated aqueous sodium chloride solution
5. 5
   Secadodried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
7. 7
   Lavado400 ml of diisopropyl ether-n-hexane (2:3), elution
8. 8
   workup.ADDITIONis carried out with 1000 ml of a 1:1 mixture of the same solvents
9. 9
   OtroThe eluate is evaporated under reduced pressure
10. 10
    Otroto remove the solvent

Procedimiento

In 30 ml of acetone is dissolved 2.6 g of n-heptanoic acid, and 10 ml of 2N-NaOH, 4.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one, 30 ml of DMF and 10 ml of water are serially added to the above solution. The mixture is refluxed for 5 hours. After cooling, 400 ml of ethyl acetate is added and the mixture is 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 400 ml of diisopropyl ether-n-hexane (2:3), 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 3.0 g of the above-identified compound as a light-yellow viscous oil.

Fuente