Potassium Carbonate → (Z)-9-((1,3-dioxoisoindolin-2-yl)methyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile

Participants

Reaction Conditions

Reaction Steps

cis-1,4-Dichloro-2-butene (0.200 g, 1.6 mmol), 2((1,3-dioxoisoindolin-2-yl)methyl)-4,5-dihydroxybenzonitrile (0.500 g, 1.7 mmol), and potassium carbonate (0.77 g, 5.6 mmol) were suspended in dry DMF (80 ml) and heated to 50° C. for 5 h. The resulting mixture was cooled to room temperature and stirred overnight, then filtered. The filtrate was diluted with ethyl acetate, washed with water (2×), brine (2×), dried (Na2SO4) and concentrated in vacuo. The resulting residue was chromatographed eluting with ethyl acetate/heptanes (50:50) to yield (Z)-9-((1,3-dioxoisoindolin-2-yl)methyl)-2,5-dihydrobenzo[b][1,4]dioxocine-8-carbonitrile as a residue. 1H NMR (CDCl3): δ 7.94-7.86 (m, 2H), 7.78-7.73 (m, 2H), 7.32 (s, 1H), 6.83 (s, 1H), 5.92-5.85 (m, 2H), 4.98 (s, 4H), 4.80 (s, 2H).

Provenance & Evidence