Hydrochloric Acid → 2-benzyl 3-tert-butyl (2RS,3RS)-5-oxotetrahydrofuran-2,3-dicarboxylate

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Reaction Steps

7.93 g of (2RS,3SR)-2-(benzyloxycarbonyl)-5-oxotetrahydrofuran-3-carboxylic acid in 75 ml of chloroform was mixed with 5.5 g of 4-dimethylaminopyridine, 8.6 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 5.7 ml of tert-butyl alcohol successively and stirred at room temperature for 60 hours. The reaction solution was poured into 1N hydrochloric acid under cooling with ice and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1] to give 6.48 g of the title compound as a white solid.

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