Citric Acid → trans-5-Tert-butoxycarbonyl-2-formylmethyltetrahydrothiophene

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Reaction Steps

To a stirred solution of trans-5-tert-butoxycarbonyl-2-cyanomethyltetrahydrothiophene (2.3 g) in diethylether (100 ml), 1M diisobutyl-aluminiumhydride dissolved in hexane (12.1 ml) is added at -30° C. and the mixture is stirred for 2 hours at -20°--10° C. 10% aqueous citric acid solution is added to the mixture and extracted with ethyl acetate - benzene (1:1). The organic layer is washed with 10% aqueous citric acid solution, water and saturated sodium chloride solution. The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give trans-5-tert-butoxycarbonyl-2-formylmethyltetrahydrothiophene.

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