Flow Synthesis of 2-Methylpyridines via α-Methylation
AbstractA series of simple 2-methylpyridines were synthesized in an expedited and convenient manner using a simplified bench-top continuous flow setup. The reactions proceeded with a high degree of selectivity, producing α-methylated pyridines in a much greener fashion than is possible using conventional batch reaction protocols. Eight 2-methylated pyridines were produced by progressing starting material through a column packed with Raney® nickel using a low boiling point alcohol (1-propanol) at high temperature. Simple collection and removal of the solvent gave products in very good yields that were suitable for further use without additional work-up or purification. Overall, this continuous flow method represents a synthetically useful protocol that is superior to batch processes in terms of shorter reaction times, increased safety, avoidance of work-up procedures, and reduced waste. A brief discussion of the possible mechanism(s) of the reaction is also presented which involves heterogeneous catalysis and/or a Ladenberg rearrangement, with the proposed methyl source as C1 of the primary alcohol. View Full-Text
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Manansala, C.; Tranmer, G.K. Flow Synthesis of 2-Methylpyridines via α-Methylation. Molecules 2015, 20, 15797-15806.
Manansala C, Tranmer GK. Flow Synthesis of 2-Methylpyridines via α-Methylation. Molecules. 2015; 20(9):15797-15806.Chicago/Turabian Style
Manansala, Camille; Tranmer, Geoffrey K. 2015. "Flow Synthesis of 2-Methylpyridines via α-Methylation." Molecules 20, no. 9: 15797-15806.