A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones (Beilstein Journal of Organic Chemistry)

Abstract The acylation of the acetonitrile anion with lactones and esters in ethereal solvents was successfully exploited using inexpensive KOt-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. Beilstein J. Org. Chem. 2019, 15, 2930–2935. doi:10.3762/bjoc.15.287