反应 #93004

ord-a12a091f133c40afb685201a87e3a710

反应方程式

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

反应物

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

试剂

无

溶剂

ClCCl
dichloromethane

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.ADDITIONare added
  2. 2
    温度The mixture is refluxed for 4 hours
  3. 3
    温度After cooling
  4. 4
    洗涤the mixture is washed with water and saturated aqueous sodium chloride solution
  5. 5
    干燥dried over anhydrous magnesium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    洗涤passage of 400 ml of diisopropyl ether and 400 ml of diisopropyl ether-ethyl acetate (10:1), elution
  8. 8
    其他The eluate is evaporated under reduced pressure
  9. 9
    其他to remove the solvent

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US04609650uspto-grants-1986_09