تفاعل #92997

ord-ba43561350ab4dbdae794445f8174128

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
O=C([O-])CCC(=O)O.[Na+]
monosodium succinate
→
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(=O)O
above-identified compound
المردود 24.5%
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(=O)O
16β-Ethyl-17β-(2-carboxyethyl)carbonyloxyacetoxy-4-estren-3-one
المردود 24.5%

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
O=C([O-])CCC(=O)O.[Na+]
monosodium succinate

الكواشف

لا شيء

المذيبات

CC(C)=O
acetone

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.DISTILLATIONThe acetone is distilled off under reduced pressure
  2. 2
    استخلاصthe residue is extracted with 150 ml of ethyl acetate
  3. 3
    أخرىThe organic layer is separated
  4. 4
    غسيلwashed with water and saturated aqueous sodium chloride solution
  5. 5
    تجفيفdried over anhydrous sodium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    غسيلpassage of 450 ml of chloroform, elution
  8. 8
    أخرىThe eluate is evaporated under reduced pressure
  9. 9
    أخرىto remove the solvent
  10. 10
    أخرىgiving colorless crystals
  11. 11
    غسيلThe product is washed with petroleum ether
  12. 12
    أخرىdried

الإجراء التجريبي

In 100 ml of 50% aqueous acetone are dissolved 1.5 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one and 0.7 g of monosodium succinate and the solution is stirred at room temperature (15°-25° C.) for 3 days. The acetone 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 sodium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. Following passage of 450 ml of chloroform, elution is carried out with 150 ml of ethyl acetate. The eluate is evaporated under reduced pressure to remove the solvent, giving colorless crystals. The product is washed with petroleum ether and dried to give 0.4 g of the above-identified compound.

المصدر

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