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The acylation of the acetonitrile anion with lactones and esters in ethereal solvents was successfully exploited using inexpensive KO t -Bu to obtain a variety of β-ketonitriles and trifunctionalized building blocks, including useful O -unprotected diols. It was discovered that lactones react to produce the corresponding derivatized cyclic hemiketals. Furthermore, the addition of a catalytic amount of isopropanol, or 18-crown-6, was necessary to facilitate the reaction and to reduce side-product formation under ambient conditions.

A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones