反応 #93009

反応方程式

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

cyclopentanecarboxylic acid

NaOH

water

→

above-identified compound

収率 106.6%

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

収率 106.6%

溶媒

acetone

反応条件

後処理

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
   抽出the residue is extracted with 150 ml of ethyl acetate
5. 5
   その他The organic layer is separated
6. 6
   洗浄washed with water and saturated aqueous sodium chloride solution
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
9. 9
   洗浄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
    その他The eluate is evaporated under reduced pressure
12. 12
    その他to remove the solvent

実験手順

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.

出典