Trifluoroacetonitrile → Methyl 4-hydroxy-6-oxo-2-(trifluoromethyl)-1,6-dihydropyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Dimethyl 1,3-acetonedicarboxylate (34.8 g, 0.2 mol) is slowly added to a solution of potassium t-butoxide (22.4 g, 0.2 mol) in THF (300 mL) at 60° C. After addition, the reaction mixture is stirred at 60° C. for 2 hours. The reaction is allowed to cool to 40° C. and trifluoroacetonitrile gas (100 g, 1.05 mol) is slowly bubbled slowly into the above mixture. The reaction temperature is maintained at 50° C. overnight. The volatile material is removed in vacuo. The residue is dissolved in water (200 mL) and the solution is poured into hydrogen chloride solution (conc. HCl/water 80 mL: 200 mL). The white solid is collected by filtration and dried. After being triturated with chloroform (200 mL), the title product is obtained as a white solid. 1H NMR: (CDCl3) 6.29 (s, 1H), 3.76 (s, 3H).

Provenance & Evidence