Ethyl 2-methylnicotinate → (2-Methylpyridin-3-yl)methanol

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Reaction Steps

To a stirred solution of ethyl 2-methylnicotinate (1.50 g, 9.09 mmol) in THF (65 mL) at 0° C. was added LAH (9.1 mL of a 1.0 M solution in THF; 9.1 mmol). The mixture was stirred at ambient temperature for 18 h and then quenched by the sequential addition of ethyl acetate (0.1 mL), water (0.1 mL), 15% aqueous NaOH (0.1 mL) and water (0.28 mL). The solids were removed by filtration through celite and the filtrate solvents were removed under reduced pressure. 3-Hydroxymethyl-2-methylpyridine was obtained as an oil (TLC: Rf = 0.40 (5:95 MeOH:CH2Cl2)).

Provenance & Evidence