Triacetoxyperiodinane → 2,6-Dichloropyridine-3-carbaldehyde

Participants

Reaction Steps

To a solution of (2,6-dichloropyridin-3-yl)methanol (1.0 g, 5.62 mmol) in CH2Cl2 (10 ml) was added Dess-Martin reagent (4.8 g, 11.24 mmol) at 26° C. After addition the mixture was stirred at room temperature for 2 h. Once the reaction was complete, the mixture was then quenched by adding 5% aqueous Na2S2O3 and stirred for 30 min. The resulting mixture was extracted with CH2Cl2 (2×30 ml). The combined organic layers were washed with saturated Na2S2O3 solution (50 ml), brine (30 ml), dried over Na2SO4 and concentrated to give the title compound which was used in next step without further purification. (800 mg, Yield 80%). 1H NMR (400 MHz, CDCl3): 10.38 (s, 1H), 8.19 (d, J=8.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H).

Provenance & Evidence