Hydrochloric Acid → HCID 66734647, compound

Participants

Reaction Conditions

Reaction Steps

4-Methoxypyridine (9.30 mL, 91.64 mmol) was dissolved in THF (150 mL) under nitrogen atmosphere and cooled to −15° C. Phenethylmagnesium chloride (93 mL, 93.47 mmol, 1 M in THF) was added dropwise and a suspension was formed. After stirring at −20° C. for 30 minutes methyl chloroformate (9.23 mL, 119.13 mmol) was added over 1 minute. Stirring was continued at −10° C. for 1 h and then HCl (10%) was added. The mixture was stirred for 20 minutes and then concentrated. The aqueous phase was extracted with ether (×2) and the organic phase was dried (MgSO4) and evaporated to yield methyl 4-oxo-2-phenethyl-3,4-dihydropyridine-1(2H)-carboxylate (21.7 g, 82%) as an oil. 1H NMR (600 MHz, cdcl3) δ 1.98 (m, 2H), 2.54 (m, 2H), 2.69 (m, 1H), 2.81 (m, 1H), 3.83 (s, 3H), 4.62 (m, 1H), 5.33 (m, 1H), 7.12-7.38 (m, 5H), 7.72 (m, 1H); MS m/z 260 (M+H)+.

Provenance & Evidence