18402-85-2Relevant articles and documents
Knoevenagel Reactions with β-Oxo Acids. Regiospecific Enol Equivalents for Syntheses of α,β-Unsaturated Ketones and of Some β-Ketols
Grayson, David H.,Tuite, Mathew R. J.
, p. 2137 - 2142 (2007/10/02)
3-Oxobutanoic acid reacts with aliphatic aldehydes in the presence of pyridine to give α,β-unsaturated methyl ketones in good yields.Analogous results were obtained with a series of other β-oxo acids.Synthesis of (E)-7-methyloct-4-en-3-one, a major constituent of the marine sponge Plakortis zygompha, has been carried out using this methodology.Aromatic aldehydes are generally less reactive under these conditions but give β-ketols when the phenyl ring bears an electron-withdrawing substituent.Some observations on the mechanism of the reaction between 3-oxobutanoic acid and benzaldehyde are presented.
