تفاعل #93009

معادلة التفاعل

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

cyclopentanecarboxylic acid

NaOH

water

→

above-identified compound

المردود 106.6%

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

المردود 106.6%

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONare added
2. 2
   درجة الحرارةThe mixture is refluxed for 6 hours
3. 3
   workup.DISTILLATIONThe solvent is distilled off under reduced pressure
4. 4
   استخلاصthe residue is extracted with 150 ml of ethyl acetate
5. 5
   أخرىThe organic layer is separated
6. 6
   غسيلwashed with water and saturated aqueous sodium chloride solution
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
9. 9
   غسيلAfter 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
    أخرىThe eluate is evaporated under reduced pressure
12. 12
    أخرىto remove the solvent

الإجراء التجريبي

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.

المصدر