Triacetoxyperiodinane → 6-Formyl-3-methylbenzofuran-2-carbonitrile

Participants

Reaction Steps

To a solution of 6-(hydroxymethyl)-3-methylbenzofuran-2-carbonitrile (116 mg, 0.62 mmol) in 6 mL of DCM was added NaHCO3 (125 mg, 1.49 mmol), followed by Dess-Martin periodinane (315 mg, 0.74 mmol). The reaction was stirred at room temperature for 1 hr. The reaction was quenched by addition of 2 mL of sat. NaHCO3 and 2 mL of sat. Na2S2O3 and stirred for 30 min. The reaction mixture was extracted with DCM (3×50 mL), the organic layer was washed with H2O, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography 100% Heptane-50% Ethyl Acetate/50% Heptane) to give 6-formyl-3-methylbenzofuran-2-carbonitrile (96 mg). 1H NMR (400 MHz, DMSO-d6) δ 2.51 (br. s., 3H), 7.97 (dd, J=8.1, 1.2 Hz, 1H), 8.04-8.09 (m, 1H), 8.27 (s, 1H), 10.14 (s, 1H).

Provenance & Evidence