Toluene → 2-Benzyloxy-3-pyridinecarbaldehyde

Participants

Reaction Steps

To a mixture of 2-(benzyloxy)nicotinonitrile (47.50 g) and anhydrous toluene (100 mL) was dropwise added a solution (1 M, 500 mL) of diisobutylaluminum hydride in hexane at −78° C. The reaction mixture was allowed to warm to room temperature with stirring for 1.5 hrs. A saturated aqueous ammonium chloride solution was dropwise added to the mixture and the mixture was stirred at room temperature for 30 min. Ethyl acetate was added to the mixture, and the mixture was further stirred at room temperature for 30 min. Insoluble materials were filtered off. The filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give 2-(benzyloxy)nicotinaldehyde as an oil (19.71 g, 41%) from a fraction eluted with ethyl acetate-hexane (1:6, v/v).

Provenance & Evidence