4-Toluenesulfonyl chloride → HCID 19835877, compound

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).

1. filtrationfiltered
2. washthe filtrate washed successively with aqueous 10% copper sulfate (50 ml), 10% aqueous sodium bicarbonate (50 ml) and saturated brine (50 ml)
3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
4. customthe solvent removed under reduced pressure
5. customThe residue was purified by column chromatography (silica gel, hexane/ethyl acetate, 70/30)

ORD record

ord-08990497a76341beab3b72241c66aa10

Source dataset

uspto-grants-1989_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04888358