Реакция #1365214

Уравнение реакции

water

4-chlorophenylacetic acid ethyl ester

1-isopropyl-2-dimethylamino-1-pyrrolinium methylsulfate

sodium

→

product

Выход 8.5%

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

Выход 8.5%

Растворители

diethyl ether

ethanol

Условия реакции

Обработка

1. 1
   workup.ADDITIONAdd [dropwise,
2. 2
   workup.ADDITIONAfter completion of the addition
3. 3
   Температураthen cool
4. 4
   ДругоеCollect the organic phase
5. 5
   Экстракцияextract the aqueous phase once again with diethyl ether
6. 6
   Другоеdry
7. 7
   Концентрированиеconcentrate them
8. 8
   Другоеto obtain
9. 9
   Другоеa yield [45.6 g (92% of theory)] of crude title compound
10. 10
    Другоеrecrystallize 5 g from ethanol/water

Методика

Add [dropwise, with stirring, at from 90°-100°, in a stream of nitrogen] a solution of 5.1 g of sodium in 100 ml of ethanol to a mixture of 32 g of 4-chlorophenylacetic acid ethyl ester and 59.13 g of 1-isopropyl-2-dimethylamino-1-pyrrolinium-methylsulfate. After completion of the addition, continue stirring for a further 30 minutes; then cool and take up with water (≈100 ml) and diethyl ether (≈150 ml). Collect the organic phase, extract the aqueous phase once again with diethyl ether, combine the ether extracts, dry and concentrate them to obtain a yield [45.6 g (92% of theory)] of crude title compound; recrystallize 5 g from ethanol/water to obtain 4.2 g of product with a m.p. of 70° to 71°.

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