Triacetoxyperiodinane → 5-(4-Chloro-benzyloxy)-4-methoxy-pyridine-2-carbaldehyde

Participants

Reaction Steps

[5-(4-Chloro-benzyloxy)-4-methoxy-pyridin-2-yl]-methanol (73, 480 mg, 1.7 mmol) was dissolved in dimethyl sulfoxide (26 mL) and Dess-Martin periodinane (909 mg, 2.1 mmol) was added. The reaction was allowed to stir at room temperature for 2 hours. The reaction was concentrated under high vacuum and then poured into a solution of NaHCO3 and Na2S2O3. The mixture was extracted with ethyl acetate. The organic portions were dried with anhydrous sodium sulfate and filtered. The filtrate was adsorbed onto silica and purified by silica gel chromatography, ethyl acetate:hexanes, to provide the desired compound as a white powder (74, 343 mg, 72%).

Provenance & Evidence