반응 #93010

반응 방정식

16β-ethyl-17β-hydroxy-4-estren-3-one

trimethylamine

2-(n-hexanoyloxy)propionyl chloride

sodium hydrogen carbonate

→

above-identified compound

16β-Ethyl-17β-(2-(n-hexanoyloxy)propionyl)oxy-4-estren-3-one

용매

dichloromethane

ethyl acetate

반응 조건

후처리

1. 1
   workup.ADDITIONis added to the solution
2. 2
   온도The mixture is refluxed for 2 hours
3. 3
   온도After cooling
4. 4
   기타The organic layer is separated
5. 5
   세척washed with water and saturated aqueous sodium chloride solution
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
8. 8
   workup.DISSOLUTIONthe residue dissolved in a small amount of diisopropyl ether
9. 9
   세척After serial passage of diisopropyl ether-n-hexane mixtures (2:8, 100 ml and 1:6, 300 ml), elution
10. 10
    workup.ADDITIONis carried out with 500 ml of a 1:1 mixture of the same solvents
11. 11
    기타The eluate is evaporated under reduced pressure
12. 12
    기타to remove the solvent

실험 절차

In 15 ml of dichloromethane are dissolved 0.75 g of 16β-ethyl-17β-hydroxy-4-estren-3-one and 0.5 ml of trimethylamine, and 0.5 ml of 2-(n-hexanoyloxy)propionyl chloride is added to the solution. The mixture is refluxed for 2 hours. After cooling, the reaction mixture is poured into a mixture of 100 ml of ethyl acetate and 30 ml of saturated aqueous sodium hydrogen carbonate solution. 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 dissolved in a small amount of diisopropyl ether. The solution is subjected to silica gel column chromatography. After serial passage of diisopropyl ether-n-hexane mixtures (2:8, 100 ml and 1:6, 300 ml), elution is carried out with 500 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 0.48 g of the above-identified compound as a light-yellow viscous oil.

출처