Реакция #51192

Уравнение реакции

4-iodoanisole

acrylonitrile

tri-o-tolylphosphine

triethylamine

→

title compound

Выход 59.5%

3-(4-Methoxyphenyl)-2-propenenitrile

Выход 59.5%

Растворители

EtOAc

ethyl acetate

ethyl acetate

pentane

pentane

acetonitrile

Условия реакции

Обработка

1. 1
   Промывкаwashed with 2M sodium hydrogen carbonate (100 ml)
2. 2
   Сушкаthe organic layer was dried over magnessium sulphate
3. 3
   Фильтрацияfiltered
4. 4
   ДругоеThe filtrate was evaporated in vacuo
5. 5
   Другоеpurified by column chromatography

Методика

A solution of 4-iodoanisole (1 g, 4.2 mmol), acrylonitrile (0.3 ml, 4.7 mmol), tri-o-tolylphosphine (243 mg, 0.4 mmol), palladium (II) acetate (90 mg, 0.4 mmol) and triethylamine (1.78 ml, 12 mmol) in acetonitrile (20 ml) was refluxed under nitrogen for 14 hours. The reaction mixture was diluted with EtOAc (50 ml) and washed with 2M sodium hydrogen carbonate (100 ml), the organic layer was dried over magnessium sulphate and filtered. The filtrate was evaporated in vacuo and purified by column chromatography using pentane, then 95:5 pentane:ethyl acetate, then 90:10 pentane:ethyl acetate to give the title compound (414 mg, 2.5 mmol) as a mixture of cis and trans isomers as yellow crystals, 1H NMR (CDCl3 400 MHz) δ: 3.8 (s, 3H), 5.7 (d, 1H), 6.9 (d, 1H), 7.2 (d, 1H), 7.4 (d, 2H); LRMS: m/z 176 (M+NH4+); Anal. Found C, 74.44; H, 5.66; N, 8.36. C10H39NO.0.1H2O requires C, 74.42; H, 5.65; N, 8.41%.

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