Ethanol → Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate

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To a mixture of ethynylcyclopentane (0.74 mL; 6.05 mmol) and ethyl 2-nitroacetate (1.37 mL; 12.11 mmol) in ethanol (9 mL) in an Ace pressure tube was added 1,4-diazobicyclo[2.2.2]octane (DABCO, 0.070 g; 0.60 mmol). The tube was heated at 80° C. for 96 h. The mixture was evaporated. The flash chromatography on silica gel (eluent: 20 to 80% dichloromethane in heptane) of the residue provided 1.21 g (96%) of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate as an oil.

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