Diethyl formamidomalonate → 1-Formyl-5-hydroxy-4-[2-nitrophenyl]-pyrrolidine-2,2-dicarboxylic acid diethylester

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Reaction Steps

To a stirred, icebath-cooled mixture of 42.5 g. (0.24 mol) of acrolein of Example 1 and 50.4 g (0.25 mol) of diethyl formamidomalonate in 200 ml. of absolute ethanol was added, over 15 minutes, 4 ml. of a 1M solution of sodium ethoxide in ethanol. The mixture was stirred at 5° for 1 hour as the Michael adduct crystallized out. After the suspension had been stored for 4 hours at -20°, the product was collected by filtration washed with ethanol (-60°) and dried to yield 82.4 g (90%) of offwhite crystals, m.p. 109-111°. The analytical sample was prepared by recrystallization from ethanol: white crystals, m.p. 113-115°.

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