Dimethylformamide → 1-(5-Methoxy-3-methyl-1-benzofuran-2-yl)-2,2-dimethylpropan-1-one

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Reaction Conditions

Reaction Steps

DMF (4 mL) was added to a mixture of 166 mg 1-(2-hydroxy-5-methoxyphenyl)ethanone and 370 mg cesium carbonate followed by 188 mg 1-bromopinacolone. After heating this mixture in an 85° C. oil bath for 3 hours, it was poured into cold water and extracted with ether. The combined ether extract was washed with water, 1.5 N NaOH, water, and saturated brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give a crude product. It was purified on silica gel (9:1 hexanes and EtOAc) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz) δ 7.41 (d, J=9.0 Hz, 1H), 7.11 (dd, J=2.5 & 9.0 Hz, 1H), 7.04 (d, J=2.5 Hz, 1H), 3.90 (s, 3H), 2.59 (s, 3H), 1.43 (s, 9H).

Provenance & Evidence