Water → 1-(4-Pyridyl)-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene

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Reaction Steps

A solution of 1-(4-pyridyl)-2,3-bis(methoxycarbonyl)-6,7-dimethoxynaphthalene (2.0 g) in tetrahydrofuran (50 ml) is added dropwise to a suspension of lithium aluminum hydride (100 mg) in tetrahydrofuran (20 ml) at -20° C. The mixture is stirred under ice-cooling for one hour, and thereto are added water (0.1 ml) and 15% aqueous sodium hydroxide solution (0.1 ml). Ten minutes thereafter, water (0.3 ml) is added to the reaction mixture, and the mixture is stirred at room temperature for one hour. The insoluble materials are removed by filtration on celite, and the filtrate is concentrated. The residue is recrystallized from a mixture of ethyl acetate and diethyl ether (1:1) to give 1-(4-pyridyl)-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (1.35 g).

Provenance & Evidence