Facile synthesis of 4-substituted pyridines using Grignard reagents was written by Akiba, Kinya;Iseki, Yuji;Wada, Makoto. And the article was included in Tetrahedron Letters in 1982.Quality Control of 4-Hexylpyridine This article mentions the following:
Reaction of N-(tert-butyldimethylsilyl)pyridinium triflate (I) with Grignard reagents gave 4-substituted 1,4-dihydropyridine derivatives with ≳99% regioselectivity; on oxidation with O these readily gave 4-substituted pyridines in 58-70% yield. E.g., treatment of I with BuMgBr in THF at room temperature under N for 2-3 h followed by bubbling O through the mixture gave 79% 4-butylpyridine. In the experiment, the researchers used many compounds, for example, 4-Hexylpyridine (cas: 27876-24-0Quality Control of 4-Hexylpyridine).
4-Hexylpyridine (cas: 27876-24-0) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Quality Control of 4-Hexylpyridine