2,6-Di-tert-butylpyridine (BDMEP) is a colorless liquid. Insoluble in water, soluble in ethanol, acetone and hexane. This reagent may be toxic and should be handled with care and performed in a fume hood.
In the gas phase, BDMEP is highly alkaline, but in solution it is weakly alkaline, due to solvation steric hindrance. Therefore, BDMEP forms a hydrochloride salt with HCl but does not react with Mel or BF3 [1].
In the synthesis of [trans-2,3-trans-5,6-d4]-1,4-dioxane and divinyl ketone, BDMEP base is used to inhibit acid-catalyzed side chain reactions Or nucleophilic reaction (Formula 1, Formula 2) [2,3].
2,6-di-tert-butylpyridine and its analogs (such as 4-methyl-BDMEP) can be used in the reaction of carbonyl compounds or trifluoromethanesulfonyl anhydride to prepare vinyl triflate. Because BDMEP combined with polymers can be reused, good experimental results can be obtained (Formula 3) [4]. The intermediate vinyl silane prepared from 2,3-dihydro-4H-pyran-4-one derivative can undergo Diels-Alder reaction with alkynes to obtain silyl phenyl ether (Formula 4) [5]. Under the action of BDMEP, condensed formaldehyde reacts with trimethylsilyl ketone ether to form β-alkoxy ketone (Formula 5) [6].
In the presence of 2,6-di-tert-butylpyridine, derivatives of allyl alcohol react with PhSeBr in methanol to produce an addition reaction of selenium and methoxy groups. This reaction has high regioselectivity. properties and stereoselectivity (Formula 6) [7,8].
References
1. Brown, H. C.; Kanner, B. J. Am. Chem. Soc., 1966, 88, 986.
2. Nakamura, E.; Kubota, K.; Isaka, M. J. Org.Chem., 1992, 57 cyclohexylamine carbonate, 5809. methylpyridine
3. (a) Wright, M. E.; Pulley, S. R. J. Org. Chem., 1987, 52, 1623.
(b) Wright, M. E.; Pulley, S. R. J. Org. Chem., 1989, 54,2886.
4. Obrecht, D. Helv. Chim. Acta., 1991, 74, 27.
5. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron, 1988, 44,4259.
6. (a) Gassman, P. G.; Singleton, D. A. J. Am. Chem. Soc., 1984,106, 7993. (b) Reynolds, D. W.; Lorenz, K. T.; Chiou, H. S.;Bellville, D. J.; Pabon, R. A. ; Bauld, N. L. J. Am. Chem. Soc., 1987, 109, 4960. (c) Schmittel, M.; Seggern, H. V. Angew. Chem. Int. Ed. Engl., 1991, 30, 999.
7. Kim, K. S.; Park, B. H.; Kim, J. Y.; Ahn, H. Y.; Jeong, I. H. Tetrahedron Lett., 1996, 37, 1249.
8. Snider, B. B.; Grabowski, J. F. Tetrahedron Lett., 2005, 46, 823.
