Iodine → 2-Benzyloxy-4,6-dimethylpyridin-3-yl 4-methoxyphenyl methanol

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Reaction Steps

A Grignard reagent (0.5 mol/L solution in tetrahydrofuran) was prepared in the usual way from 4-bromoanisole, magnesium, a catalytic amount of iodine and tetrahydrofuran. The obtained Grignard reagent (0.41 mL) was added to a solution of 2-benzyloxy-3-formyl-4,6-dimethylpyridine (0.019 g) in tetrahydrofuran (0.8 mL), and the mixture was stirred for 80 minutes at room temperature. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=4/1) to give 2-benzyloxy-4,6-dimethylpyridin-3-yl 4-Methoxyphenyl methanol (0.014 g) To a solution of the obtained 2-benzyloxy-4,6-dimethylpyridin-3-yl 4-methoxyphenyl methanol (0.014 g) in ethanol (1 mL) was added a catalytic amount of 10% palladium carbon powder, and the mixture was stirred for 2 hours at room temperature under a hydrogen atmosphere. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (developing solvent: dichloromethane/methanol=10/1) to give 3-(4-methoxybenzyl)-4,6-dimethyl-1H-pyridin-2-one (0.010 g).

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