Abstract
Diethoxyphosphorylmethyl derivatives of furancarboxylic acids react with thionyl chloride in the presence of DMF to form the corresponding acid chlorides. Compounds synthesized were reduced with sodium borohydride in the DMF-dioxane medium to give hydroxymethyl compounds. Obtained phosphorylated alcohols were oxidized to aldehydes by chromium trioxide-pyridine complex in methylene chloride. The diethoxyphosphorylmethyl group remains untouched in all these transformations. A series of phosphorylated acid chlorides, alcohols, and aldehydes including all six versions of mutual location of phosphorus-containing substituent and another functional group in the furan ring was synthesized. It is established that 2,3- and 3,2-(diethoxyphosphorylmethyl)(chlorocarbonyl)furans in the course of vacuum distillation undergo cyclization to 4,5(2,3-furo)- and 4,5(3,2-furo)-1,2-oxaphosphorines.
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