반응 #93004

ord-a12a091f133c40afb685201a87e3a710

반응 방정식

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

반응물

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

시약

없음

용매

ClCCl
dichloromethane

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.ADDITIONare added
  2. 2
    온도The mixture is refluxed for 4 hours
  3. 3
    온도After cooling
  4. 4
    세척the mixture is washed with water and saturated aqueous sodium chloride solution
  5. 5
    건조dried over anhydrous magnesium sulfate
  6. 6
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  7. 7
    세척passage of 400 ml of diisopropyl ether and 400 ml of diisopropyl ether-ethyl acetate (10:1), elution
  8. 8
    기타The eluate is evaporated under reduced pressure
  9. 9
    기타to remove the solvent

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04609650uspto-grants-1986_09