تفاعل #93004

ord-a12a091f133c40afb685201a87e3a710

معادلة التفاعل

CCOC(C)=O
ethyl acetate
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)CO
16β-ethyl-17β-glycoloyloxy-4-estren-3-one
CC(=O)[O-].[Na+]
sodium acetate
C=C1CC(=O)O1
diketene
→
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)CC(C)=O
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)CC(C)=O
16β-Ethyl-17β-(3-oxobutyryl)oxyacetoxy-4-estren-3-one

المتفاعلات

CCOC(C)=O
ethyl acetate
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)CO
16β-ethyl-17β-glycoloyloxy-4-estren-3-one
CC(=O)[O-].[Na+]
sodium acetate
C=C1CC(=O)O1
diketene

الكواشف

لا شيء

المذيبات

ClCCl
dichloromethane

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONare added
  2. 2
    درجة الحرارةThe mixture is refluxed for 4 hours
  3. 3
    درجة الحرارةAfter cooling
  4. 4
    غسيلthe mixture is washed with water and saturated aqueous sodium chloride solution
  5. 5
    تجفيفdried over anhydrous magnesium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    غسيلpassage of 400 ml of diisopropyl ether and 400 ml of diisopropyl ether-ethyl acetate (10:1), elution
  8. 8
    أخرىThe eluate is evaporated under reduced pressure
  9. 9
    أخرىto remove the solvent

الإجراء التجريبي

In 30 ml of dichloromethane is dissolved 0.8 g of 16β-ethyl-17β-glycoloyloxy-4-estren-3-one, and 0.24 g of anhydrous sodium acetate and 0.3 ml of diketene are added. The mixture is refluxed for 4 hours. After cooling, 100 ml of ethyl acetate is added and the mixture is 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. Following serial passage of 400 ml of diisopropyl ether and 400 ml of diisopropyl ether-ethyl acetate (10:1), elution is carried out with 600 ml of isopropyl ether-ethyl acetate (2:3). The eluate is evaporated under reduced pressure to remove the solvent, giving 1.0 g of the above-identified compound as a light-yellow viscous oil.

المصدر

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