Hydrochloric Acid → Dipyridin-3-ylmethanol

Temperature

-60 °C

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%).

1. stirringthe mixture was stirred at a temperature of −60° C. to −15° C. for 30 minutes
2. washby washing with saturated sodium bicarbonate and brine
3. dry with materialdrying over anhydrous sodium sulfate
4. customThe solvent was evaporated off under reduced pressure
5. customthe residue was purified by preparative thin-layer chromatography (chloroform/methanol=12/1)

ORD record

ord-b72fcd15d42248db8ec68c1227474b96

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673908B2