Water → 6-Hydroxymethyl-3-(p-methoxybenzyl)oxy-1-(p-methoxybenzyl)-4-pyridone

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Reaction Steps

To a suspension of 2.613 g of 6-hydroxymethyl-3-(p-methoxybenzyl)oxy-4-pyridone in 100 ml of dimethyl-formamide were added sequentially 2.073 g of potassium carbonate and 2.35 g of p-methoxybenzyl chloride, and the mixture is stirred at room temperature for 40 hours. The reaction mixture is added to 200 ml of water and 400 ml of dichloromethane, and the organic layer is washed with 200 ml of water. The organic layer is dried over anhydrous magnesium sulfate, condensed under reduced pressure and subjected to flash column chromatography on 100 g of Wako-Gel C-300 (manufactured by Wako Pure Chemical Industries, Ltd.) with an eluent of chloroformmethanol (20:1) to perform separation and purification. 6-hydroxymethyl-3-(p-methoxybenzyl)oxy-1-(p-methoxybenzyl)-4-pyridone and 6-hydroxymethyl-3,4-bis[(p-methoxybenzyl)oxy]-pyridine are obtained as colorless crystals in amounts of 1.749 g and 1.527 g, respectively. 6-hydroxymethyl-3-(p-methoxybenzyl)oxy-1-(p-methoxybenzyl)-4-pyridone;

Provenance & Evidence