تفاعل #51192

معادلة التفاعل

4-iodoanisole

acrylonitrile

tri-o-tolylphosphine

triethylamine

→

title compound

المردود 59.5%

3-(4-Methoxyphenyl)-2-propenenitrile

المردود 59.5%

المذيبات

EtOAc

ethyl acetate

ethyl acetate

pentane

pentane

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with 2M sodium hydrogen carbonate (100 ml)
2. 2
   تجفيفthe organic layer was dried over magnessium sulphate
3. 3
   ترشيحfiltered
4. 4
   أخرىThe filtrate was evaporated in vacuo
5. 5
   أخرىpurified by column chromatography

الإجراء التجريبي

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%.

المصدر