Levulinic acid esters cleavage

Esterification, crotonic acid, 149 levulinic acid, 157 thiophene-2-carboxylic acid, 182 o-toluic acid, 162 Ester interchange, 152 Ethanolysis of ethyl iminoacetate, 159 Ether cleavage with HBr, 271... 

Reactions with functionalized alkyl halides significantly enhance the range of application of alkyl [ C]acetoacetates. Alkylation of ethyl [3- C]acetoacetate with halo esters, for example, followed by acid-mediated ketonic cleavage opens access to labeled keto acids/esters, as demonstrated by the synthesis of the [4- C]levulinic acid (307) a y-keto acid. The latter has served as a key intermediate in the synthesis of the 2,3-substituted indole 308 . Step 2 in Figure 6.85, the ketonic cleavage, has recently been shown to be accelerated by a factor of 20 when the reaction is submitted to microwave heating. ... 

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