Abstract
Ethyl 2-methylfuran-3-carboxylate is smoothly chloroethylated at 0°C in the 5 position of the ring. The resulting halide alkylates secondary amines but eliminates HCl with sodium diethyl phosphite under the Michaelis-Becker reaction conditions and with trimethyl phosphite under the Arbuzov reaction conditions. In the reaction with sodium diethyl phosphite, small amounts of 5-[1-(diethoxyphosphoryl)ethyl]furan-3-carboxylate and 5-ethylfuran-3-carboxylate are formed. In the Arbuzov reaction at a 1: 1.22 furan: trimethyl phosphite molar ratio, methyl 2,4-dimethyl-1-methoxy-1-oxo-1λ5-1,2-dihydrophospheto[3,2-b]furan-5-carboxylate was isolated.
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Original Russian Text © L.M. Pevzner, 2007, published in Zhurnal Obshchei Khimii, 2007, Vol. 77, No. 1, pp. 120–124.
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Pevzner, L.M. Synthesis and selected reactions of ethyl 5-(1-chloroethyl)-2-methylfuran-3-carboxylate. Russ J Gen Chem 77, 111–115 (2007). https://doi.org/10.1134/S107036320701015X
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DOI: https://doi.org/10.1134/S107036320701015X