Reacción #51192

Ecuación de reacción

4-iodoanisole

acrylonitrile

tri-o-tolylphosphine

triethylamine

→

title compound

Rendimiento 59.5%

3-(4-Methoxyphenyl)-2-propenenitrile

Rendimiento 59.5%

Disolventes

EtOAc

ethyl acetate

ethyl acetate

pentane

pentane

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 2M sodium hydrogen carbonate (100 ml)
2. 2
   Secadothe organic layer was dried over magnessium sulphate
3. 3
   Filtraciónfiltered
4. 4
   OtroThe filtrate was evaporated in vacuo
5. 5
   Otropurified by column chromatography

Procedimiento

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%.

Fuente