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

HRID 431772

반응식

HRID 431772 반응식
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

참가 물질

9

반응물 4

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

생성물 1

HCID 342403-(4-Methoxyphenyl)prop-2-enenitrile수율 59.5%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매HCID 8003Pentane용매2회HCID 8857Ethyl Acetate용매3회

실험 절차

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. C10H39NO0.1H2O requires C, 74.42; H, 5.65; N, 8.41%.

후처리

  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

출처 및 근거

ORD 기록
ord-ef3ca741ccc248fe937aebd9d82650da
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660756B2

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