Potassium Carbonate → (S)-1-(tert-butyldimethylsilyloxy)pent-4-yn-2-ol

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Reaction Steps

Potassium carbonate (1.5 eq) is added to a solution of (R)-1-(tert-butyldimethylsilyloxy)-5-(trimethylsilyl)pent-4-yn-2-ol (1 eq) in methanol and the mixture stirred at room temperature for 8 hours. The solvent is removed under reduced pressure and aqueous ammonium chloride solution added. The mixture is extracted with ethyl acetate (3×) and the combined organic layers washed with brine, dried (MgSO4), concentrated under reduced pressure and purified by flash chromatography (biotage) using a gradient of EtOAc in hexane.

Provenance & Evidence