Methyl morpholine oxide → Ethyl 3-formylimidazo[1,2-a]pyridine-2-carboxylate

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Reaction Steps

A solution of 1.2 g (5.45 mmol) of ethyl 3-(hydroxymethyl)-imidazolo[1,2-a]pyridine-2-carboxylate in 50 mL dichloromethane is treated with 1.75 g (15.0 mmol) of N-methylmorpholine N-oxide, 2.5 g powdered 4A molecular sieves and 180 mg (0.5 mmol) tetrapropylammonium perruthenate. The mixture is stirred at room temperature for 2 hr and applied directly to a column of silica. The column is eluted with 10% methanol in dichloromethane to afford 1.09 g (92%) ethyl 3-formyl-imidazolo[1,2-a]pyridine-2-carboxylate.

Provenance & Evidence