Sodium hydride → Ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetate

Participants

Reaction Steps

Sodium hydride (60% dispersion in mineral oil; 63 mg) was added to a solution of compound D (254 mg) in DMF (5 ml). When evolution of hydrogen ceased, a solution of compound C (500 mg) in DMF (5 ml) was added and the solution was left to stand for 20 hours. Water (50 ml) was added and the mixture was extracted with ethyl acetate (2×25 ml). The combined extracts were washed with water (25 ml), followed by saturated sodium chloride solution (25 ml) and then dried (MgSO4). The solvent was removed by evaporation and the residue purified by flash chromatography, eluting with ethyl acetate/hexane (1:1 v/v), to give ethyl 2-[4-((2-ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl)phenoxy]phenylacetate (A) (265 mg), as an oil which solidified on standing, m.p. 89°-90° C. (after trituration with hexane); NMR: 1.1-1.35(2×t, 6H), 1.7-1.9(m, 4H), 2.6(t, 2H), 2.7(q, 2H), 2.85(t, 2H), 4.1-4.3(m, 2H), 5.0(s, 2H), 5.6(s, 1H), 6.5(s, 1H), 7.0(d, 2H), 7.25-7.5(m, 5H), 7.55-7.65(m, 2H).

Provenance & Evidence