Ethyl (4-chlorophenyl)acetate → 2-(alpha-Ethoxycarbonyl-4-chlorobenzylidene)-1-methylpyrrolidine

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Reaction Steps

Add [dropwise, with stirring, at 100° (bath temperature), in a stream of nitrogen] a solution of 9.6 g of sodium in 200 ml of ethanol to a mixture of 99 g of 2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate and 65 g of 4-chlorophenylacetic acid ethyl ester. Remove the alcohol from the reaction mixture by the stream of nitrogen. Continue stirring for a further 30 minutes at 100°; cool the reaction mixture; add 200 ml of water to the cooled reaction mixture; and then extract it with 5×100 ml of diethyl ether. Combine the ether extracts, dry the combined extracts over sodium sulfate, concentrate them and then remove a little excess 4-chlorophenylacetic acid ethyl ester by heating under a high vacuum to obtain a yield [86 g (94% of theory)] of crude title compound having a m.p. of 71°.

Provenance & Evidence