Pyridines with 2,4-alkyl groups have acidic hydrogens in the neighboring position of the ring. These hydrogens can be removed by using strong bases such as tert-butyllithium, LDA, etc.

alkyl vinyl pyridines 01

The base obtained has an important nucleophilic character, which allows the chain to be lengthened by attacking different electrophiles.


a) Attack on primary haloalkanes

alkyl vinyl pyridines 02

b) Attack on carbonyls

alkyl vinyl pyridines 03

c) Attack on oxacyclopropanes

alkyl vinyl pyridines 04