Abstract
A synthetic approach to 2-alkoxycarbonyl-3-indolealkanoic acidsvia partial saponification of the corresponding diesters is presented. 2-Ethoxycarbonyl-3-indoleacetic acid as well as the homologous propionic and butyric acids may conveniently be prepared by this method. A different synthesis of 3-indoleacetic acids functionalized at position 2 can be accomplished by decomposition of ethyl diazoacetate in the presence of the indole derivative at elevated temperature. Cyclization of 2-hydroxymethyl-3-indoleacetic acid, thus prepared, yields the corresponding δ-valerolactone. With 1-acyl-indoles and ethyl diazoacetate addition of the carbene to the C-2=C-3 double bond prevails, resulting in the formation of cyclopropanecarboxylic esters.
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Keller, H., Langer, E. & Lehner, H. Synthesen 2-substituierter 3-Indol-alkansäuren. Monatshefte für Chemie 108, 123–131 (1977). https://doi.org/10.1007/BF00900914
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DOI: https://doi.org/10.1007/BF00900914