Tetrahydrofuran → 1alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-methyleneandrost-5-ene

Temperatur

60 °C

A mixture of tetrahydrofuran (70 ml), methyltriphenylphosphonium bromide (50 g) and potassium t-butoxide (13.9 g) were stirred at 60° C. for 2 hours, while under suspension. To this suspension, was added 1α,3β-bis(tert-butyldimethylsilyloxy)androst-5-ene (18.7 g) and tetrahydrofuran (60 ml), followed by reaction for 2 hours under reflux. Under cooling with ice, the reaction mixture was slowly added to a cooled mixture of hexane (200 ml) and water (100 ml) to stop the reaction. The organic layer was washed with saturated brine twice, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent, giving crude crystals (27 g). The crude crystals were mixed with hexane (100 ml), stirred at room temperature while under suspension. After filtering off insoluble material from the suspension, the filtrate was evaporated under reduced pressure to remove the solvent, giving crude crystals, which were then dissolved in acetone (80 ml) by stirring at room temperature. The mixture was mixed with methanol (160 ml) and stirred at room temperature; the thus precipitated crystals were collected by filtration and dried to give the titled compound (13.2 g).

1. customfollowed by reaction for 2 hours
2. temperatureunder reflux
3. temperatureUnder cooling with ice
4. customthe reaction
5. washThe organic layer was washed with saturated brine twice
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated under reduced pressure
8. customto remove the solvent
9. customgiving crude crystals (27 g)
10. stirringstirred at room temperature while under suspension
11. filtrationAfter filtering off insoluble material from the suspension
12. customthe filtrate was evaporated under reduced pressure
13. customto remove the solvent
14. customgiving crude crystals, which
15. stirringby stirring at room temperature
16. stirringstirred at room temperature
17. filtrationthe thus precipitated crystals were collected by filtration
18. customdried

ORD-Eintrag

ord-cf7db74464e144219f9c73c4d6f70138

Quelldatensatz

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07074777B2