Hydrochloric Acid → 6-(1,1-Dimethylethyl)-2-pyridinecarboxaldehyde

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Reaction Steps

Diisobutylaluminum hydride (1.02 mol/L toluene solution, 23.5 mL, 24.1 mmol) was added to a solution of 6-tert-butylpyridine-2-carbonitrile obtained (2.57 g, 16.0 mmol) in tetrahydrofuran (20 mL) under a nitrogen atmosphere at −78° C., and the mixture was stirred for 1.5 hr while cooling in ice. To the reaction mixture was added 1 mol/L hydrochloric acid, and the mixture was diluted with ethyl acetate and stirred at room temperature for 45 min. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane only→hexane:ethyl acetate=4:1) to afford the title compound as a yellow oil (1.71 g).

Provenance & Evidence