Tetrahydrofuran → 4-(furan-2-carbonyl)-3,4-dihydroquinoxalin-2(1H)-one

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Reaction Steps

2-Furoyl chloride (0.49 ml) is added to a solution of the 1,2,3,4-tetrahydroquinoxalin-2-one (IV, EXAMPLE 1, 710 mg), triethylamine (0.80 ml), and THF (20.0 ml) at 0°. The mixture is stirred for 1.5 hr at 0° and for 2 hr at 20°-25°. The mixture was diluted with aq. sodium bicarbonate and extracted with ethyl acetate and chloroform several times. The organic phases are combined, dried with magnesium sulfate, concentrated, and recrystallized from hot ethyl acetate to give the title compound, mp 229°-230°; IR (mineral oil) 2954, 2925, 1684, 1648, 1504, 1474, 1391, 1373 and 756 cm-1 ; NMR (CDCl3) 8.53, 7.39, 7.1-7.25, 6.85-7.05, 6.45 and 4.59 δ; MS (m/z) 242 and 95.

Provenance & Evidence