Benzyl Bromide → HCID 12089327, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-hydroxy-4-ethoxycarbonyl-6-methyl-2-pyridinone (prepared by the method of Feist et al., Chem. Ber., 1902, vol. 35, p. 1545; 23.9 g, 121 mmol) and benzyl bromide (14.4 mL, 121 mmol) in DMF (400 mL) at 0° C. was added cesium carbonate (39.7, 121 mmol). The resulting mixture was stirred at 4° C. for 48 h. More benzyl bromide was added (2.8 mL, 24 mmol) and the mixture was stirred at 4° C. for another 72 h. The solvent was removed in vacuo and the residue was suspended in CH2Cl2. The solids were removed by filtration and the filtrate solvent was removed in vacuo. The residue was purified by flash column chromatography using 1:3 EtOAc:hexanes as eluant to give the title compound (18 g; HPLC RT=15.04 min, method B).

Provenance & Evidence