Diethyl Malonate → Ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate

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Reaction Steps

At room temperature, 1 ml of a solution of 0.71 g of diethyl malonate in tetrahydrofuran was added to a mixture of 0.19 g of sodium hydride and 4 ml of tetrahydrofuran, and the mixture was stirred for 20 minutes. At room temperature, 3 ml of a solution of 0.59 g of 3,4-dimethyl-2H-1,3-oxazine-2,6(3H)-dione in tetrahydrofuran was added to the mixture, followed by stirring for 2 hours under heat refluxing condition. The reaction mixture was concentrated under reduced pressure. To the residue were added 10 ml of water and 12 ml of 2 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and concentrated to obtain 0.57 g of ethyl 1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate represented by the formula:

Provenance & Evidence