Sodium Sulfate → 2-Methoxy-3-hydroxymethyl-5-ethyl-6-methylpyridine

Participants

Reaction Steps

To a solution of methyl 2-methoxy-5-ethyl-6-methylnicotinate (2.28 g, 10.9 mmol) in anhydrous tetrahydrofuran (50 mL), under a nitrogen atmosphere, was added cautiously lithium aluminum hydride (0.77 g, 20 mmol). After refluxing this mixture for 15-20 hours, saturated aqueous Na2SO4 was added carefully to quench the cooled reaction mixture. This mixture was diluted with more THF, dried (Na2SO4), filtered and the solvent evaporated. This residue was chased with ethanol/toluene to remove traces of water and triturated with hexane as the product slowly crystallized out to give 1.30 g (66%), mp 53°-55° C.

Provenance & Evidence