Water → 16beta-Ethyl-17beta-cyclopentanecarbonyloxyacetoxy-4-estren-3-one

HRID 64731

반응식

HRID 64731 반응식
[CH:1]1([C:6]([OH:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].O.[CH2:12]([C@H:14]1[CH2:19][C@H:18]2[C@H:20]3[C@H:29]([CH2:30][CH2:31][C@:16]2([CH3:17])[C@H:15]1[O:33][C:34](=[O:37])[CH2:35]Br)[C@@H:28]1[C:23](=[CH:24][C:25](=[O:32])[CH2:26][CH2:27]1)[CH2:22][CH2:21]3)[CH3:13]>CC(C)=O>[CH2:12]([C@H:14]1[CH2:19][C@H:18]2[C@H:20]3[C@H:29]([CH2:30][CH2:31][C@:16]2([CH3:17])[C@H:15]1[O:33][C:34](=[O:37])[CH2:35][O:7][C:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:8])[C@@H:28]1[C:23](=[CH:24][C:25](=[O:32])[CH2:26][CH2:27]1)[CH2:22][CH2:21]3)[CH3:13]

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18840Cyclopentanecarboxylic acidHCID 1559376416beta-Ethyl-17beta-bromoacetoxy-4-estren-3-one

생성물 1

HCID 7046776316beta-Ethyl-17beta-cyclopentanecarbonyloxyacetoxy-4-estren-3-one수율 106.6%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

In 40 ml of acetone is dissolved 0.6 g of cyclopentanecarboxylic acid, and 6.0 ml of 1N-NaOH and 16 ml of water are added, followed by addition of 1.2 g of 16β-ethyl-17β-bromoacetoxy-4-estren-3-one. The mixture is refluxed for 6 hours. The solvent is distilled off under reduced pressure and the residue 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 magnesium sulfate. The solvent is then distilled off under reduced pressure and the residue is subjected to column chromatography. After serial passage of diisopropyl ether-n-hexane mixtures (1:9, 200 ml; 2:8, 200 ml; and 3:7, 200 ml), elution is carried out with 800 ml of a 1:1 mixture of the same solvents. The eluate is evaporated under reduced pressure to remove the solvent, giving 1.38 g of the above-identified compound as a colorless viscous oil.

후처리

  1. additionare added
  2. temperatureThe mixture is refluxed for 6 hours
  3. distillationThe solvent is distilled off under reduced pressure
  4. extractionthe residue is extracted with 150 ml of ethyl acetate
  5. customThe organic layer is separated
  6. washwashed with water and saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent is then distilled off under reduced pressure
  9. washAfter serial passage of diisopropyl ether-n-hexane mixtures (1:9, 200 ml; 2:8, 200 ml; and 3:7, 200 ml), elution
  10. additionis carried out with 800 ml of a 1:1 mixture of the same solvents
  11. customThe eluate is evaporated under reduced pressure
  12. customto remove the solvent

출처 및 근거

ORD 기록
ord-6ce408e79760438eb42ae9b3d072b4b6
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04609650

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