Hydrochloric Acid → 2-Cyano-2-methylhexyl p-toluenesulfonate

Participants

Reaction Steps

535 mg (3.8 mM) of (+)-2-cyano-2-methylhexanol ([α]D26 +0.66 degree (c 1.823, ether)) and 911 mg (11.4 mM) of dry pyridine were stirred at room temperature, and 724 mg (3.8 mM) of p-toluenesulfonyl chloride was added thereto, followed by 7 hours of reaction. After the reaction, 3 ml of 2N-hydrochloric acid was added thereto, followed by extraction with diethyl ether. the resultant organic layer was washed with a small amount of 2N-hydrochloric acid and distilled water, followed by drying on sodium sulfate, distilling-off of the solvent and purification by silica gel column chromatography (developer solvent: methylene chloride) to obtain 748 mg of 2-cyano-2-methylhexyl p-toluenesulfonate (yield: 63.3%).

Provenance & Evidence