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

HRID 431772Notes

Reaction equation

HRID 431772 reaction equation
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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8003PentaneSolvent2×HCID 8857Ethyl AcetateSolvent3×

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-ef3ca741ccc248fe937aebd9d82650da
Source dataset
uspto-grants-2003_12
Patent number
US06660756B2

Reaction notes

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