Water → 4-Toluenesulfonyl chloride

Participants

Reaction Steps

To a solution of 9.255 g (51.07 mmol) of the above 2-[allyl-(3-furylmethyl)amino]ethanol, 10.7 ml (76.6 mmol) of triethylamine and 0.1 g of 4-dimethylaminopyridine in 150 ml of dichloromethane, 11.7 g (61.3 mmol) of p-toluenesulfonyl chloride was added at room temperature, followed by overnight stirring at room temperature. The reaction mixture was poured into water and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 9/1) to yield N-allyl-N-(3-furylmethyl)-2-chloroethylamine as a mixture with p-toluenesulfonyl chloride.

Provenance & Evidence