Efficient Synthesis of (E)-3-Alkylidene-2(3H)-furanones from 3-(1-Hydroxy­alkyl)-2-silyloxyfurans

Several unsubstituted (E)-3-alkylmethylidene- and (E)-3-(arylmethylidene)-2(3H)-furanones have been synthesized in highly stereoselective fashion by mesylation-elimination of 3-(1-hydoxyalkyl)-2-silyloxyfurans. The latter were prepared from 2triisopropylsilyloxy-3-bromofuran by halogen-lithium exchange and reaction of the in situ generated 3-lithiated silyloxyfuran with aldehydes.