Uses
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.
Synthesis
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 ).
