Acetic Acid → Diethyl 2-(5-methoxy-2,3-dihydrobenzofuran-6-yliden)-malonate

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Reaction Steps

To a solution of 5-Methoxy-2,3-dihydrobenzofuran-6-al (295 mg, 1.66 mmol) in benzene was added diethyl malonate (265 mg, 1.66 mmol), acetic acid (20 mL, 0.35 mmol) and piperidine (30 mL, 0.30 mmol). The mixture was heated at reflux for 3 h and then poured into 100 mL of water. This mixture was extracted with three 50 mL portion of ethyl acetate. The combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure gave quatitative yield of the title compound as a yellowish oil: 1H NMR (400 MHz, CDCl3) d 8.02 (s, 1 H), 6.79 (s, 1 H), 6.78 (s, 1 H), 4.52 (t, 2 H), 4.30 (m, 4 H), 3.80 (s, 3 H), 3.18 (t, 2 H), 1.28 (m, 6 H).

Provenance & Evidence