Reaktion #1102148

Reaktionsgleichung

methanesulfonyl chloride

potassium thioacetate

1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene

triethylamine

→

titled compound

Ausbeute 88.3%

17-acetylthiomethyl-1α,3β-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene

Ausbeute 88.3%

Lösungsmittel

hexane

dimethyl sulfoxide

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 30 minutes
2. 2
   Waschenwashed with water
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   SonstigeAfter evaporation under reduced pressure
5. 5
   Sonstigeto remove the solvent
6. 6
   Sonstigethe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

Vorschrift

To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (4.00 g, 7.34 mmol) in tetrahydrofuran (70 ml), triethylamine (4.10 ml, 29.4 mmol) was added and methanesulfonyl chloride (1.70 ml, 22.0 mmol) was further added dropwise at −10° C., followed by stirring for 20 minutes. After warming to room temperature, a solution of potassium thioacetate (3.73 g, 29.4 mmol) in dimethyl sulfoxide (70 ml) was added to the reaction mixture. The reaction mixture was stirred for 30 minutes, diluted with hexane, washed with water and then dried over anhydrous magnesium sulfate. After evaporation under reduced pressure to remove the solvent, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give the titled compound (3.91 g, 88%) as a colorless oil.

Quelle