Diethyl Ether → HCID 20651890, compound

Participants

Reaction Steps

To a solution of 8-hydroxynaphthalene-1-(N,N-dimethyl)carboxamide (68 mg, 0.32 mmol) in dry DMF (4 mL) was added sodium hydride (8 mg, 0.35 mmol, 1.1 eq). The sodium hydride was added as 14 mg of a 60% dispersion in mineral oil that had been previously washed with 3×heptane portions under an inert atmosphere. The mixture was stirred for 30 minutes at room temperature and 1-chloro-(4-biphenyl)methanol (71 mg, 0.35 mmol, 1.1 eq) was added. The resulting mixture was stirred at room temperature overnight. The reaction mixture was poured onto ice/water (100 mL), and the aqueous-DMF layer was extracted into ethyl acetate portions. The combined organic layers were washed (brine), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, eluant:ethyl acetate/heptane mixtures) to give the desired ether (yield: 99 mg, 0.25 mmol, 79%);

Provenance & Evidence