4-Hydroxy-6-methyl-2-pyrone

white to light yellow crystal powder

4-Hydroxy-6-methylpyran-2-one was used in the synthesis of pyrano[3,2-c]pyridones with antiproliferative and apoptosis inducing activities. It was also used in the design of benzisothiazolone human leukocyte elastase inhibitors.

ChEBI: Triacetate lactone is a member of 2-pyranones. It is a conjugate acid of a triacetate lactone oxoanion.

Synthetic Communications, 20, p. 1931, 1990 DOI: 10.1080/00397919008053123

14.4g (0.1mol) isopropylidene malonate, 35ml dichloromethane and 15ml chlorobenzene were placed in the reaction flask, cooled to <5C under stirring, 10.1g (0.1mol) triethylamine and 10.1g (0.12mol) bis(vinylidene) ketone were added dropwise. After addition, slowly warmed to room temperature, continue to stir for 2 hours. The reaction was washed with cooled dilute hydrochloric acid, dried, filtered and most of the dichloromethane was removed in a rotary evaporator. The residual reactant was heated and refluxed for 2 hours, and yellow crystals were precipitated. The crystals were cooled, filtered and washed with a small amount of ether. After drying, 4-hydroxy-6-methyl-2-pyranone was obtained 10.1g, yield 82%, m.p. 186-189 (literature value 188-189 ).