2-Fluoropyridine → (4-(Pyridin-2-yloxymethyl)-phenyl)-methanol

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1,4-benzenedimethanol (5.5 g, 40 mmol), 2-fluoropyridine (1.3 g, 13 mmol) and N,N-dimethylformamide (15 mL) was added sodium hydride (1.4 g, 40 mmol, 66% in oil) at 0° C., which was stirred for 20 minutes at room temperature and for 1 hour at 70° C. To the reaction mixture was added water, and extraction was performed with ethyl acetate. The organic layer was washed with saturated saline, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1) to obtain the titled compound (1.9 g, 66%).

Provenance & Evidence