反应 #93009

反应方程式

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

cyclopentanecarboxylic acid

NaOH

water

→

above-identified compound

收率 106.6%

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

收率 106.6%

溶剂

acetone

反应条件

后处理

1. 1
   workup.ADDITIONare added
2. 2
   温度The mixture is refluxed for 6 hours
3. 3
   workup.DISTILLATIONThe solvent is distilled off under reduced pressure
4. 4
   萃取the residue is extracted with 150 ml of ethyl acetate
5. 5
   其他The organic layer is separated
6. 6
   洗涤washed with water and saturated aqueous sodium chloride solution
7. 7
   干燥dried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
9. 9
   洗涤After 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
    其他The eluate is evaporated under reduced pressure
12. 12
    其他to remove the solvent

实验过程

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.

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