Benzyl Bromide → 1-Benzyl-3-methyl-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester

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Reaction Conditions

Reaction Steps

A flask was charged with 3-methyl-6-oxo-1,6-dihydro-pyridine-2-carboxylic acid ethyl ester (230 mg, 1.27 mmol), toluene (6.4 mL) and water (0.064 mL). K2CO3 (351 mg, 2.54 mmol), LiBr (221 mg, 2.54 mmol), tetrabutylammonium bromide (41 mg, 0.127 mmol), and benzyl bromide (0.23 mL, 1.91 mmol) were added, and the resulting suspension was heated at 80° C. for 40 min. The mixture was allowed to come to r.t., diluted with CH2Cl2, and filtered. The filtrate was concentrated in vacuo, and the residue was chromatographed (0-10% MeOH/CH2Cl2) to give 158 mg of the title compound as a viscous oil. MS: (+) m/z 272.31 (M+1).

Provenance & Evidence