Toluene → (2-Chloropyridin-3-yl)methanol

Participants

Reaction Steps

At −78° C., diisobutylaluminum hydride (a 1.0M toluene solution; 4.68 ml) was added dropwise to a methylene chloride (10 ml) solution of ethyl 2-chloronicotinate (347 mg, 1.87 mmol). Thirty minutes later, the reaction mixture was ice cooled, followed by stirring for 15 minutes. After the completion of the reaction was confirmed, brine was added to the reaction mixture and the temperature of the resulting mixture was allowed to rise back to room temperature. The reaction mixture was filtered through Celite. The filtrate was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column and the fraction obtained from the hexane:ethyl acetate (=1:1) eluate was concentrated under reduced pressure, whereby the title compound (211 mg, 79%) was obtained as a white solid.

Provenance & Evidence