A novel approach to the synthesis of 4-aryl-furan-3-ols

A novel, yet simple, method for the synthesis of 4-aryl-furan-3-ols is described. The condensation between dimethyl diglycolate 1 and various aryl glyoxylates 2 using KOt-Bu as base furnished a series of 4-aryl-furan-3-ols 4 bearing one tert-butyl ester and one methyl ester substituent. Such a mixed ester allowed easy differentiation of the two esters for selective chemical modification. In addition, these 4-aryl-furan-3-ols could be further transformed to other useful substituted furans through conversion to the triflates and subsequent metal-mediated reduction or coupling.