Sodium periodate → Methyl 5-formylpyrazine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of the 5-(2-dimethylamino-vinyl)-pyrazine-2-carboxylic acid methyl ester (415 mg, 2.0 mmol) in tetrahydrofuran and water (10 mL, 1:1) was treated with powdered sodium periodate (1.3 g, 6.07 mmol). The mixture was stirred at 25° C. for 30 min, at which time, thin layer chromatography suggested complete conversion to a product less polar than starting material. The reaction mixture was concentrated in vacuo nearly to dryness, and the residue was partitioned with ethyl acetate (50 mL) and a saturated aqueous sodium bicarbonate solution (25 mL). The aqueous phase was extracted with ethyl acetate (2×50 mL). Each of the organic extracts was washed with a saturated aqueous sodium chloride solution (25 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to afford the crude aldehyde, 5-formyl-pyrazine-2-carboxylic acid methyl ester (180 mg), as an orange oil which was used without further characterization or purification.

Provenance & Evidence