반응 #93009

반응 방정식

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

cyclopentanecarboxylic acid

NaOH

water

→

above-identified compound

수율 106.6%

16β-Ethyl-17β-cyclopentanecarbonyloxyacetoxy-4-estren-3-one

수율 106.6%

용매

acetone

반응 조건

후처리

1. 1
   workup.ADDITIONare added
2. 2
   온도The mixture is refluxed for 6 hours
3. 3
   workup.DISTILLATIONThe solvent is distilled off under reduced pressure
4. 4
   추출the residue is extracted with 150 ml of ethyl acetate
5. 5
   기타The organic layer is separated
6. 6
   세척washed with water and saturated aqueous sodium chloride solution
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
9. 9
   세척After serial passage of diisopropyl ether-n-hexane mixtures (1:9, 200 ml; 2:8, 200 ml; and 3:7, 200 ml), elution
10. 10
    workup.ADDITIONis carried out with 800 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 40 ml of acetone is dissolved 0.6 g of cyclopentanecarboxylic acid, and 6.0 ml of 1N-NaOH and 16 ml of water are added, followed by addition of 1.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 6 hours. The solvent is distilled off under reduced pressure and the residue is extracted with 150 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. After serial passage of diisopropyl ether-n-hexane mixtures (1:9, 200 ml; 2:8, 200 ml; and 3:7, 200 ml), elution is carried out with 800 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.38 g of the above-identified compound as a colorless viscous oil.

출처