Hydrochloric Acid → benzyl 4-oxo-2-phenyl-3,4-dihydropyridine-1(2H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

4-Methoxypyridine (1-1, 0.7 g, 6.4 mmol) in anhydrous THF at −20° C. was treated with 3-methoxyphenyl magnesium bromide (14.1 mL, 7.0 mmol) and benzyl chloroformate (1.09 g, 6.4 mmol) and stirred 4 h at −20° C. The reaction was poured into 1N HCl and stirred 10 min. The reaction mixture was extracted with Et2O (50 mL), washed with brine and dried over MgSO4. The organic extracts were filtered, concentrated under reduced pressure and purified viaflash column chromatography (SiO2, 0-50% EtOAc-hexanes gradient) to give benzyl 4-oxo-2-phenyl-3,4-dihydropyridine-1(2H)-carboxylate (1-2). MS 338.1 found 338.4 (M+H+) required.

Provenance & Evidence