4-Toluenesulfonyl chloride → HCID 86672618, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, 55 mL (0.39 mol) of triethylamine, 59.9 g (0.314 mol) of p-toluenesulfonyl chloride, and 2.5 g (26 mmol) of trimethylamine hydrochloride were added to a solution of 85.0 g (0.262 mol) of 5,9,13,17-tetramethyloctadec-4-en-1-ol in dry methylene chloride (0.26 L) at 0° C., sequentially. After being stirred for 1 hour, 9.9 mL (79 mmol) of N,N-dimethyl-1,3-propanediamine was added to the reaction solution at 0° C. After being stirred for 1 hour, the mixture was diluted with a mixed solvent of hexane/ethyl acetate. The resulting solution was washed with water, 3M hydrochloric acid (twice), saturated sodium bicarbonate aqueous solution, and saturated brine, successively, and dried over magnesium sulfate. After filtration, the filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=90:10) to obtain 116 g of (5,9,13,17-tetramethyloctadec-4-enyl)tosylate (93% yield).

Provenance & Evidence