반응 #92993

ord-4e73e6cc4d934006ac75e1e1b528d289

반응 방정식

CCCCCCCCCCCCCC(=O)O
myristic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
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
→
CCCCCCCCCCCCCC(=O)OCC(=O)O[C@H]1[C@@H](CC)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C
above-identified compound
수율 63.9%
CCCCCCCCCCCCCC(=O)OCC(=O)O[C@H]1[C@@H](CC)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21C
16β-Ethyl-17β-myristoyloxyacetoxy-4-estren-3-one
수율 63.9%

반응물

CCCCCCCCCCCCCC(=O)O
myristic acid
O=C([O-])[O-].[K+].[K+]
potassium carbonate
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

시약

없음

용매

CC(C)=O
acetone

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도The mixture is refluxed for 5 hours
  2. 2
    온도After cooling
  3. 3
    추출the reaction mixture is extracted with 150 ml of ethyl acetate
  4. 4
    기타The organic layer is separated
  5. 5
    세척washed with water and saturated aqueous sodium chloride solution
  6. 6
    건조dried over anhydrous sodium sulfate
  7. 7
    workup.DISTILLATIONThe solvent is then distilled off under reduced pressure
  8. 8
    세척the residue is subjected to column chromatography, elution
  9. 9
    기타The eluate is evaporated under reduced pressure
  10. 10
    기타to remove the solvent
  11. 11
    기타giving a light-yellow viscous oil
  12. 12
    기타to stand at room temperature
  13. 13
    기타(15°-25° C.)

실험 절차

To 100 ml of 30% aqueous acetone are added 1.0 g of myristic acid and 0.8 g of potassium carbonate, followed by addition of 1.16 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 5 hours. After cooling, the reaction mixture 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, elution being carried out with 600 ml of toluene-diisopropyl ether (19:1). The eluate is evaporated under reduced pressure to remove the solvent, giving a light-yellow viscous oil. This product is allowed to stand at room temperature (15°-25° C.) to give 1.0 g of the above-identified compound as a solid.

출처

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