Triacetoxyperiodinane → 5-Acetyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

Participants

Reaction Steps

Treat a solution of 5-(1-hydroxyethyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester (250 mg, 0.85 mmol) in dichloromethane (10 mL) with Dess-Martin periodinane (470 mg, 1.11 mmol). Stir at room temperature for 2.5 h, quench with 10% aqueous sodium sulfate, extract with ethyl acetate (50 mL). Wash with 10% aqueous sodium sulfate solution, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes) to give the title compound (196 mg, 78%).

Provenance & Evidence