Estradiol → HCID 10599968, 화합물

HRID 460475

반응식

HRID 460475 반응식
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][C:15]=3[C@H:5]1[CH2:4][CH2:3]2.[H-].[Na+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C)C=O>[CH2:23]([O:20][C:18]1[CH:17]=[CH:16][C:15]2[C@@H:5]3[C@H:6]([C@H:7]4[C@@:2]([CH2:3][CH2:4]3)([CH3:1])[C@@H:10]([O:11][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:8]4)[CH2:12][CH2:13][C:14]=2[CH:19]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

5

반응물 3

HCID 5757EstradiolHCID 7498Benzyl BromideHCID 24758Sodium hydride

생성물 1

HCID 10599968HCID 10599968, 화합물수율 190%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Dimethylformamide (11 ml) was added to β-estradiol (1.08 g, 4.0 mmol) under nitrogen atmosphere, followed by cooling on ice. Sodium hydride (480 mg of 60% suspension) was added to the reaction mixture followed by stirring for 10 minutes on ice and then stirred for 1 hour at room temperature. After cooling again on ice, Benzyl bromide (2.05 g, 12 mmol) was added to the reaction mixture followed by stirring for 10 minutes on ice and then stirred for 20 hours at room temperature. The reaction mixture was quenched with ice-cold water and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure using an evaporator and the resulting residue was triturated with methanol to precipitate solids. The solids were collected by filtration and vacuum dried to give 3,17β-bis(benzyloxy)estra-1,3,5(10)-triene (1.72 g, Yield 95%).

후처리

  1. temperatureby cooling on ice
  2. stirringstirred for 1 hour at room temperature
  3. additionwas added to the reaction mixture
  4. stirringby stirring for 10 minutes on ice
  5. stirringstirred for 20 hours at room temperature
  6. customThe reaction mixture was quenched with ice-cold water
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water and saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. customan evaporator
  13. customthe resulting residue was triturated with methanol
  14. customto precipitate solids
  15. filtrationThe solids were collected by filtration and vacuum
  16. customdried

출처 및 근거

ORD 기록
ord-509049e2bdc4412bb6ae4c1a21d709c9
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196081B2

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