Tetrabutylammonium Fluoride → 5,7-diethyl-1-(4-hydroxy-3-propylbenzyl)-1,6-naphthyridin-2(1H)-one

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Reaction Steps

1.0M Tetrabutylammonium fluoride in tetrahydrofuran (2 ml) was added to a stirred solution of compound E (0.9 g) in tetrahydrofuran (8 ml) under an atmosphere of argon. The solution was left to stand for 2 hours and then volatile material was removed by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate, to give 5,7-diethyl-1-(4-hydroxy-3-propylbenzyl)-1,6-naphthyridin-2(1H)-one (F) (0.54 g) as a foam; NMR: 0.9(t, 3H), 1.2(t, 3H), 1.3(t, 3H), 1.55-1.65(m, 2H), 2.55(t, 2H), 2.8(q, 2H), 3.1(q, 2H), 5.4(s, 2H), 5.5(br s, 1H), 6.65(d, 1H), 6.75(d, 1H), 6.9(d, 1H), 6.95(s, 1H), 7.05(s, 1H), 7.95(d, 1H).

Provenance & Evidence