Sodium hydride → Methyl 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carboxylate

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Reaction Steps

Sodium hydride (60% dispersion in mineral oil; 60 mg) was added to a stirred solution of 2-ethyl-4-quinolone (260 mg) prepared by the method described in Org. Syn., 1955, Coll. Vol. III, p.374 and p593), in N,N-dimethylformamide (DMF)(2.5 ml). The mixture was stirred until evolution of hydrogen had ceased and then a solution of the bromomethyl compound (C) (460 mg) in DMF (1 ml) was added. The reaction mixture was stirred for 16 hours. The solvent was removed by evaporation and the residue was partitioned between water (10 ml) and ethyl acetate (2×5 ml). The organic phase was washed with water, followed by saturated sodium chloride solution and dried (MgSO4). The solvent was evaporated and the residue purified by flash chromatography, eluting with ethyl acetate/dichloromethane (1:4 v/v) to give methyl 4'-[(2-ethylquinolin-4-yloxy)methyl]biphenyl-2-carboxylate (A) as a solid (385 mg), m.p. 132°-134° C.; NMR: 1.41(t,3H), 2.97(q,2H), 3.68(s,3H), 5.34(s,2H), 6.77(s,1H), 7.44-7.7(complex m,9H), 7.87(dd,1H), 8.0(d,1H), 8.26(dd,1H); mass spectrum (positive chemical ionisation [+ve CI]: 398 (M+H)+, 225, 174; 13C NMR: (benzylic CH2) 69.73.

Provenance & Evidence