Nukleophile Acylierung über Glycidnitrile

Abstract

Carbonylcompounds 1, 2-chloroacrylonitrile and alkoxides react in a three-component-condensation with formation of glycidonitriles 2. 2-Cyclohexylidenexpoxi-3-methoxy-propionitrile 5 e. g. is obtained in 85% yield from cyclohexanone, 2-chloroacrylonitrile and sodium-methoxide. Glycidonitriles are useful intermediates for the synthesis of α,α'-difunctionalised ketones. 5 e. g. is easily transformed into the corresponding α-methoxy-α'-hydroxyketone 8, the α-inethoxy-α',β'-unsaturated ketone 9, the α-methoxy-α'-chloroketone 10, the α-methoxyketone 11 as well as the butenolide 12.