تفاعل #92989

ord-c0bcc5bcb0684d198df1fd0993d5e832

معادلة التفاعل

CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
CC(C)CCC(=O)O
4-methylvaleric acid
→
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)CCC(C)C
above-identified compound
CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)COC(=O)CCC(C)C
16β-Ethyl-17β-(4-methylvaleryl)oxyacetoxy-4-estren-3-one

المتفاعلات

CC[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]2(C)[C@H]1OC(=O)CBr
16β-ethyl-17β-bromoacetoxy-4-estren-3-one
CC(C)CCC(=O)O
4-methylvaleric acid

الكواشف

لا شيء

المذيبات

CC(C)=O
acetone
[Na+].[OH-]
NaOH

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةThe mixture is refluxed for 6 hours
  2. 2
    workup.DISTILLATIONThe acetone is distilled off under reduced pressure and 10 ml of water
  3. 3
    workup.ADDITIONis added to the residue
  4. 4
    استخلاصfollowed by extraction with 100 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 sodium sulfate
  8. 8
    workup.DISTILLATIONThe solvent is then distilled off
  9. 9
    غسيلthe residue is subjected to column chromatography, elution
  10. 10
    أخرىThe eluate is evaporated under reduced pressure
  11. 11
    أخرىto remove the solvent

الإجراء التجريبي

In 35 ml of acetone is dissolved 1.0 ml of 4-methylvaleric acid, and 4.6 ml of 2N-NaOH and then 1.9 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one are added to the above solution. The mixture is refluxed for 6 hours. The acetone is distilled off under reduced pressure and 10 ml of water is added to the residue, followed by extraction with 100 ml of ethyl acetate. The organic layer is separated, washed with water and saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is then distilled off and the residue is subjected to column chromatography, elution being carried out with 600 ml of diisopropyl ether-n-hexane (1:1). The eluate is evaporated under reduced pressure to remove the solvent, giving 1.3 g of the above-identified compound as a colorless viscous oil.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04609650uspto-grants-1986_09