Acrylonitrile → 3-(4-Methoxyphenyl)prop-2-enenitrile

HRID 22914

反応式

HRID 22914 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10](#[N:13])[CH:11]=[CH2:12].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCC>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:12]=[CH:11][C:10]#[N:13])=[CH:3][CH:4]=1

参加物

9

反応物 4

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 696764-IodoanisoleHCID 80271Tri-o-tolylphosphine

生成物 1

HCID 342403-(4-Methoxyphenyl)prop-2-enenitrile収率 59.5%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒HCID 8003Pentane溶媒2 回HCID 8857Ethyl Acetate溶媒3 回

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%.

後処理

  1. washwashed with 2M sodium hydrogen carbonate (100 ml)
  2. dry with materialthe organic layer was dried over magnessium sulphate
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. custompurified by column chromatography

出典と根拠

ORDレコード
ord-c1bd88a8906b45068f0e62552c375619
出典データセット
uspto-grants-2005_02
特許番号
US06849649B2

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