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

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).

1. customThe reaction was quenched by addition of 2 mL of sat. NaHCO3 and 2 mL of sat. Na2S2O3
2. stirringstirred for 30 min
3. extractionThe reaction mixture was extracted with DCM (3×50 mL)
4. washthe organic layer was washed with H2O, brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified by silica gel flash chromatography 100% Heptane-50% Ethyl Acetate/50% Heptane)

ORD record

ord-147ab4e51593428ead189da8250fd0c7

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255093B2