Triacetoxyperiodinane → 5-(Pyridin-3-yl)thiophene-2-carbaldehyde

Participants

Reaction Steps

To a solution of (5-pyridin-3-yl-thiophen-2-yl)-methanol (144 mg in 7.5 mL dry methylene chloride) was added 327 mg of the 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one and the mixture stirred at room temperature. After 4 hours, the reaction was quenched by addition of a mixture of saturated sodium bicarbonate and saturated sodium thiosulfite (1:1) and extracted with diethyl ether. The aqueous portion was extracted further with methylene chloride and the combined organics then washed with water and brine and dried over magnesium sulfate. Purification of the concentrate by flash chromatography on silica gel (ethyl acetate:hexane, 75:25; then 80:20) gave the title compound (80 mg).

Provenance & Evidence