Hydrochloric Acid → Dipyridin-3-ylmethanol

Participants

Reaction Conditions

Reaction Steps

A 1.55 mol/L solution of n-butyllithium in hexane (2.24 mL, 3.48 mmol) was added to toluene (6 mL) and the mixture was cooled to −60° C. under a nitrogen atmosphere. To this, a toluene solution (2 mL) of 3-bromopyridine (500 mg, 3.16 mmol) was added dropwise and the mixture was stirred for 30 minutes. Tetrahydrofuran (2 mL) and nicotinaldehyde (0.358 mL, 3.79 mmol) were added to the reaction mixture and the mixture was stirred at a temperature of −60° C. to −15° C. for 30 minutes. After 4 mol/L hydrochloric acid (2.37 mL, 9.48 mmol) was added to the reaction mixture, extraction with ethyl acetate was performed, followed by washing with saturated sodium bicarbonate and brine, and drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by preparative thin-layer chromatography (chloroform/methanol=12/1) to give dipyridin-3-ylmethanol (Compound EP) (235 mg, yield: 40%).

Provenance & Evidence