Uses
Methyl 2-formyl-3-oxo-propanoate is used for [2 + 2] cycloaddition (de Mayo reaction); [4 + 2]cycloaddition (hetero-Diels-Alder reaction with inverse electron demand); transformation to enamino aldehydes and their photochemical and thermal cycloadditions; Wittig reaction.
Preparation
Methyl 2-formyl-3-oxo-propanoate is prepared by Panizzi's formylation procedure of commercially available methyl 3,3- dimethoxypropanoate with methyl formate, by diformylation of potassium monomethyl malonate with dimethyl formamide and phosphorus oxychloride followed by decarboxylation, and by ozonolysis of dimethyl 2,5-cyclohexadiene-1,4-dicarboxylate.
storage
Methyl 2-formyl-3-oxo-propanoate is stable for at least 6 months if stored at -20 °C; it is a highly acidic compound. Use in a fume hood.
Purification Methods
Fractional vacuum distillation.
