Triacetoxyperiodinane → HCID 86732739, compound

Participants

Reaction Steps

To a suspension of 1-ethyl-3-(hydroxymethyl)-6,7-bis((4-methoxybenzyl)oxy) cinnolin-4(1H)-one (1.6 g, 3.36 mmol) in dichloromethane (DCM) (50 mL) at room temperature was added Dess-Martin periodinane (1.709 g, 4.03 mmol). The white suspension turned into a dark green solution. The reaction was stirred at room temperature for 1 h, treated with sodium bicarbonate solution and extracted with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by automatic silica gel column chromatography (Combiflash RF), eluting with ethyl acetate/hexanes (0-100%) to afford 1-ethyl-6,7-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydrocinnoline-3-carbaldehyde (0.9 g, 1.897 mmol, 56.5% yield) as a yellow solid. LCMS: (M+H)+: 475.2

Provenance & Evidence