Diethyl Ether → Methyl 5-(hydroxymethyl)nicotinate

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Reaction Steps

1.67 g of dimethyl pyridine-3,5-dicarboxylate was dissolved in 30 ml of anhydrous tetrahydrofuran, and with stirring under ice cooling, 162 mg of lithium aluminium hydride was added. The mixture was stirred at this temperature for 30 minutes. The reaction mixture was poured into ice water, and ethyl ether was added to extract it. The extract was worked up in a customary manner to give crude methyl 5-hydroxymethylnicotinate. The crude product was dissolved in 20 ml of methylene chloride, and 2.2 g of pyridinium chlorochromate was added. The mixture was stirred overnight at room temperature. The reaction mixture was poured into ice water. The organic layer was separated, worked up in a customary manner, and purified by silica gel column chromatography Wakogel C-200, 80 g; eluting solvent: chloroform/methanol=20/1) to give 0.37 g (yield 26%) of

Provenance & Evidence