Hydrochloric Acid → (-)-2-Cyano-2-methylpentyl p-toluenesulfonate

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Reaction Steps

In a round-bottomed flask, 1.35 mg (10.6 mM) of (-)-2-cyano-2-methylpentanol was dissolved in 2.52 g of dry pyridine. The mixture was placed on an ice bath, and 2.22 g (11.7 mM) of p-toluenesulfonyl chloride was added, followed by 6 hours of stirring at room temperature. After the reaction, 10 ml of 6N-hydrochloric acid was added, followed by 3 times of extraction with 15 ml of diethyl ether. The extract was dried overnight on anhydrous sodium sulfate, followed by distilling-off of the solvent and purification by column chromatography by using 80 g of silica gel and a dichloromethane/benzene (2/1) solvent to obtain (-)-2-cyano-2-methylpentyl p-toluenesulfonate. Yield: 2.57 g (9.1 mM), 86%

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