5-(1-Hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 2,6-diethyl-4-hydroxy-3-Pyridinecarboxylic acid methyl ester

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Reaction Conditions

Reaction Steps

A mixture of methyl 3-amino-2-pentenoate (7.3 g) and 5-(1-hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (23.0 g) was heated at 120° C. for 2 hours. The residue was cooled to ambient temperature, triturated with ether and the solid collected by filtration to give methyl 2,6-diethyl-1,4-dihydro-4-oxopyridine-3carboxylate (5.2 g) as a pale yellow solid, m.p. 124°-127° C.; NMR (d6 -DMSO): 1.2(t,6H), 2.3-2.6(m,4H), 3.7(s,3H), 6.3(s,1H); mass spectrum (chemical ionisation, ammonia): 210 (M+H)+.

Provenance & Evidence