Diethyl Oxalate → Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate

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Reaction Steps

2-acetylfuran was slowly added to a solution of sodium ethoxide (6.81 g) dissolved in absolute ethanol (200 mL) at 0° C. (5.01 mL). This solution was stirred at 0° C. for 2 hrs before oxalic acid diethyl ester (9.30 mL) was slowly added thereto. After stirring for 18 hrs, the reaction was terminated with 1N HCl. The resulting solution was concentrated under reduced pressure to remove the ethanol, followed by extraction with methylene chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 10.0 g of 4-furan-2-yl-2,4-dioxo-butyric acid ethyl ester. This concentrate was used in the next step without further purification.

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