肉豆蔻酸 → 16beta-Ethyl-17beta-myristoyloxyacetoxy-4-estren-3-one

HRID 64715

反应方程式

HRID 64715 反应方程式
[C:1]([OH:16])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].[CH2:23]([C@H:25]1[CH2:30][C@H:29]2[C@H:31]3[C@H:40]([CH2:41][CH2:42][C@:27]2([CH3:28])[C@H:26]1[O:44][C:45](=[O:48])[CH2:46]Br)[C@@H:39]1[C:34](=[CH:35][C:36](=[O:43])[CH2:37][CH2:38]1)[CH2:33][CH2:32]3)[CH3:24]>CC(C)=O>[CH2:23]([C@H:25]1[CH2:30][C@H:29]2[C@H:31]3[C@H:40]([CH2:41][CH2:42][C@:27]2([CH3:28])[C@H:26]1[O:44][C:45](=[O:48])[CH2:46][O:15][C:1](=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C@@H:39]1[C:34](=[CH:35][C:36](=[O:43])[CH2:37][CH2:38]1)[CH2:33][CH2:32]3)[CH3:24]

参与物

5

反应物 3

HCID 11005肉豆蔻酸HCID 11430碳酸钾HCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

产物 1

HCID 7046748616beta-Ethyl-17beta-myristoyloxyacetoxy-4-estren-3-one收率 63.9%

试剂、催化剂与溶剂 1

HCID 180丙酮溶剂

实验过程

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.

后处理

  1. temperatureThe mixture is refluxed for 5 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture is extracted with 150 ml of ethyl acetate
  4. customThe organic layer is separated
  5. washwashed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent is then distilled off under reduced pressure
  8. washthe residue is subjected to column chromatography, elution
  9. customThe eluate is evaporated under reduced pressure
  10. customto remove the solvent
  11. customgiving a light-yellow viscous oil
  12. customto stand at room temperature
  13. custom(15°-25° C.)

来源与证据

ORD记录
ord-4e73e6cc4d934006ac75e1e1b528d289
来源数据集
uspto-grants-1986_09
专利号
US04609650

关联笔记

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