反応 #51192
ord-c1bd88a8906b45068f0e62552c375619
反応方程式
反応条件
後処理
- 1洗浄washed with 2M sodium hydrogen carbonate (100 ml)
- 2乾燥the organic layer was dried over magnessium sulphate
- 3ろ過filtered
- 4その他The filtrate was evaporated in vacuo
- 5その他purified by column chromatography
実験手順
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%.