- Reaction of isomeric (alkoxymethyl)(chloromethyl)-and bis(chloromethyl)furans with sodium diethyl phosphite
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Reduction of alkyl (alkoxymethyl)furancarboxylates with lithium aluminum hydride leads to (alkoxymethyl)(hydroxymethyl)furans, while the reaction with structurally related acetoxymethyl derivatives yields bis(hydroxymethyl)furans. Treatment of the latter with thionyl chloride in ether in the presence of pyridine in the cold gives corresponding chloromethyl-or bis(chloromethyl)furans. These products react with sodium dialkyl phosphite under conditions of the Michaelis-Becker reaction to form mono-or diphosphonates, respectively. The yield of phosphorylated compounds is determined mainly by thermal stability of the substrate. In the case of 2,4-bis(chloromethyl)furan, nucleophilic substitution competes with halophilic attack on the chloromethyl group in the 4 position of the furan ring. As a result, a 2:1 mixture of 2-and 2,4-phosphorylated products is formed.
- Pevzner,Ignat'ev,Ionin
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