Реакция #55701

Уравнение реакции

sodium

water

title compound

2-dimethylamino-1-methyl-4,5,6,7-tetrahydro-3H-azepinium methylsulfate

ethyl 4-chlorophenylacetate

→

title compound

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

Растворители

ethyl alcohol

diethyl ether

Условия реакции

Обработка

1. 1
   workup.ADDITIONAdd (drop by drop at 90° in a stream of nitrogen
2. 2
   workup.ADDITIONMix
3. 3
   Другоеcollect the organic phase
4. 4
   Сушкаdry the latter over sodium sulfate
5. 5
   КонцентрированиеConcentrate the dried organic phase
6. 6
   Другоеdistil off any excess ethyl 4-chlorophenylacetate under a high vacuum
7. 7
   Другоеto obtain a crude

Методика

Add (drop by drop at 90° in a stream of nitrogen to let the alcohol escape) a solution of 4.6 g of sodium in 100 ml of ethyl alcohol to a mixture of 53.2 g of the title compound of Example 1 and 29.8 g of ethyl 4-chlorophenylacetate. Stir it for a further 4 hours at 90° and then cool it to ambient temperature. Mix the cooled reaction mixture with 100 ml of water and 100 ml of diethyl ether, collect the organic phase and dry the latter over sodium sulfate. Concentrate the dried organic phase and then distil off any excess ethyl 4-chlorophenylacetate under a high vacuum to obtain a crude yield [15.5 g (34% of theory)] of the title compound as yellow oil.

Источник