Water → 2-phenyl-3-methyl-8-(1-(S)-methanesulfonyloxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline

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Reaction Steps

2 ml (26 mmol) of mesyl chloride and 4 ml (27 mmol) of triethylamine are added sequentially, at 0° C., to a solution of 7 g (17.8 mmol) of 2-phenyl-3-methyl-8-(1-(S)-hydroxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline in 200 ml of ethyl ether. The solution rapidly turns cloudy and a white precipitate is formed. After stirring for one hour at ambient temperature, 150 ml of distilled water are added to the reaction medium and the aqueous phase is extracted with 3×200 ml of ethyl ether. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum to provide 8.4 g of 2-phenyl-3-methyl-8-(1-(S)-methanesulfonyloxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline in the form of a colorless oil, used without purification in the following stage. (Yield: quantitative)

Provenance & Evidence