Hydrochloric Acid → 5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

5-Methoxy-2-(4-methoxyphenyl)-benzofuran-4-carbonitrile 134 (0.088 g, 0.31 mmol) was placed in a sealed tube along with pyridine hydrochloride (enough to fill the volume of the tube by one-half) and heated at 200° C. for 2.5 hours. The reaction was dissolved into a mixture of ethyl acetate and 1N HCl. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×). The combined organics was washed with 1N HCl (1×), water (1×) and then dried over magnesium sulfate, filtered and concentrated. The resulting material was purified by column chromatography, using 40% ethyl acetate in hexanes as the eluent to yield the desired product 135 (0.066 g, 84.7%) as a light brown solid: Mp>230° C.; 1H NMR (DMSO-d6) δ 10.89 (s, 1 H), 10.03 (s, 1 H), 7.82 (d, 2 H, J=8.6 Hz), 7.72 (d, 1 H, J=8.9 Hz), 7.27 (s, 1 H), 6.90 (d, 2 H, J=8.6 Hz), 6.88 (d, 1 H, J=8.9 Hz).

Provenance & Evidence