4-Toluenesulfonyl chloride → HCID 19835877, compound

Participants

Reaction Steps

To a solution of [3-hydroxymethyl-1-hydroxycyclopent-3-en-2-yl]acetic acid, Ʊ-lactone, the compound of formula (1), (188 mg, 1.22 mmol) in 10 ml of methylene chloride was added 4-dimethylaminopyridine (119 mg, 0.97 mmol), followed by p-toluenesulfonyl chloride (280 mg, 1.46 mmol) and triethylamine (123 mg, 1.22 mmol). After stirring for 2 hours at room temperature, the mixture was diluted with diethyl ether (80 ml), filtered and the filtrate washed successively with aqueous 10% copper sulfate (50 ml), 10% aqueous sodium bicarbonate (50 ml) and saturated brine (50 ml). The organic layer was dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography (silica gel, hexane/ethyl acetate, 70/30) to give 165 mg of [3-chloromethyl-1-hydroxycyclopent-3-en-2-yl]acetic acid, Ʊ-lactone, m.p. 33°-34° C., the compound of formula (2).

Provenance & Evidence