Reaktion #722210

Reaktionsgleichung

1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-hydroxypregna-5,7,16-triene

pyridinium dichromate

Florisil

→

title compound

Ausbeute 57.6%

1α,3β-bis(tert-butyldimethylsilyloxy)-20-oxopregna-5,7,16-triene

Ausbeute 57.6%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeultrasonicated for 2.5 hours
2. 2
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
3. 3
   workup.ADDITIONthe resulting residue was diluted with diethyl ether
4. 4
   Filtrationfiltered through Celite
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   Sonstigethe resulting residue was purified by column chromatography (hexane:ethyl acetate=15:1)

Vorschrift

A suspension of 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-hydroxypregna-5,7,16-triene (600 mg, 1.07 mmol), pyridinium dichromate (610 mg, 1.61 mmol) and Florisil (3 g) in dichloromethane (10 ml) was stirred at room temperature for 1.5 hours, then ultrasonicated for 2.5 hours. The solvent was distilled off under reduced pressure and the resulting residue was diluted with diethyl ether and filtered through Celite. The solvent was distilled off under reduced pressure and the resulting residue was purified by column chromatography (hexane:ethyl acetate=15:1) to give the title compound as a colorless solid (343 mg, 57%).

Quelle