Реакция #1365212

Уравнение реакции

sodium

2-dimethylamino-1-methyl-1-pyrrolinium methylsulfate

4-chlorophenylacetic acid ethyl ester

→

crude title compound

2-(α-ethoxycarbonyl-4-chlorobenzylidene)-1-methylpyrrolidine

Растворители

ethanol

Условия реакции

Обработка

1. 1
   workup.ADDITIONAdd [dropwise,
2. 2
   ДругоеRemove the alcohol from the reaction mixture by the stream of nitrogen
3. 3
   workup.STIRRINGContinue stirring for a further 30 minutes at 100°
4. 4
   Температураcool the reaction mixture
5. 5
   workup.ADDITIONadd 200 ml of water
6. 6
   Другоеto the cooled reaction mixture
7. 7
   Экстракцияand then extract it with 5×100 ml of diethyl ether
8. 8
   Сушкаdry the combined extracts over sodium sulfate
9. 9
   Концентрированиеconcentrate them
10. 10
    Другоеremove a little excess 4-chlorophenylacetic acid ethyl ester
11. 11
    Температураby heating under a high vacuum
12. 12
    Другоеto obtain

Методика

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°.

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