Reaktion #722209

Reaktionsgleichung

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

tetra-n-butylammonium fluoride

→

title compound

Ausbeute 99.1%

1α,3β-dihydroxy-20(S)-(3-hydroxy-3-methylbutyloxy)pregna-5,7,16-triene

Ausbeute 99.1%

Lösungsmittel

ethyl acetate

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith heating
2. 2
   Temperaturunder reflux for 2 hours
3. 3
   Waschenwashed with saturated aqueous sodium bicarbonate solution and brine successively
4. 4
   Trocknenthe organic layer was dried over magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   Sonstigethe resulting residue was purified by preparative thin layer chromatography (0.5 mm×1 and 0.25 mm×1, dichloromethane

Vorschrift

A solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-20(S)-(3-hydroxy-3-methylbutyloxy)pregna-5,7,16-triene (27 mg, 0.0419 mmol) in tetrahydrofuran (1 ml) was combined with 1M tetra-n-butylammonium fluoride solution in tetrahydrofuran (0.25 ml, 0.25 mmol), and stirred at room temperature for 20 hours, then with heating under reflux for 2 hours. The reaction solution was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution and brine successively, and the organic layer was dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by preparative thin layer chromatography (0.5 mm×1 and 0.25 mm×1, dichloromethane:ethanol=20:1, developed twice) to give the title compound as a colorless oil (17.3 mg, 99%).

Quelle