Reaktion #547657

Reaktionsgleichung

Sodium hydride

β-estradiol

Benzyl bromide

→

3,17β-bis(benzyloxy)estra-1,3,5(10)-triene

Ausbeute 190.0%

Lösungsmittel

Dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturby cooling on ice
2. 2
   workup.STIRRINGstirred for 1 hour at room temperature
3. 3
   workup.ADDITIONwas added to the reaction mixture
4. 4
   workup.STIRRINGby stirring for 10 minutes on ice
5. 5
   workup.STIRRINGstirred for 20 hours at room temperature
6. 6
   SonstigeThe reaction mixture was quenched with ice-cold water
7. 7
   Extraktionextracted with ethyl acetate
8. 8
   WaschenThe organic layer was washed with water and saturated aqueous sodium chloride
9. 9
   Trocknendried over anhydrous magnesium sulfate
10. 10
    Filtrationfiltered
11. 11
    EinengenThe filtrate was concentrated under reduced pressure
12. 12
    Sonstigean evaporator
13. 13
    Sonstigethe resulting residue was triturated with methanol
14. 14
    Sonstigeto precipitate solids
15. 15
    FiltrationThe solids were collected by filtration and vacuum
16. 16
    Sonstigedried

Vorschrift

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%).

Quelle