Nitromethane → Ethyl 3-(4-chlorophenyl)-4-nitrobutanoate

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The solution of ethyl 4-chlorocinnamate (12.6 g) and N,N,N′,N′-tetramethylguanidine (1.2 g) in nitromethane (36.6 g) was kept at rt for three days. The excess of nitromethane was evaporated and the residue dissolved in diethyl ether (250 ml). The organic layer was washed with 2M HCl (2×150 ml), dried (sodium sulfate), and evaporated. The residue was subjected to purification by flash chromatography on silica gel (petrol ether/ethyl acetate 10:1) to give ethyl 3-(4-chlorophenyl)-4-nitrobutanoate (15.1 g) as yellowish oil.

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