Methyl acetoacetate → Dimethyl 2,6-dimethyl-4-[2-(3-thienyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate

Participants

Reaction Steps

To a solution of crude Compound 2c (10.6 mmol) in methanol (10 mL) was added methyl acetoacetate (10.6 mmol), methyl 3-aminocrotonate (10.6 mmol) and concentrated ammonium hydroxide (1 drop). The reaction mixture was heated at reflux under nitrogen for 4 days. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel eluted with diethyl ether:hexane (2:1) and trituration with diethyl ether:hexane (1:2) to yield Compound 2d as a pale yellow solid (m.p. 164°-166° C.).

Provenance & Evidence