Styrene → (E)-6-[2-(Phenyl)ethenyl]-2-naphthalenecarbonitrile

HRID 1384182Notes

Reaction equation

HRID 1384182 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[C:12]([C:17]#[N:18])[CH:11]=[CH:10]2)(=O)=O.[CH2:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[C:23]1(/[CH:22]=[CH:21]/[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH:13]=[C:12]([C:17]#[N:18])[CH:11]=[CH:10]3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 7501StyreneHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 155418226-Cyano-2-naphthyl trifluoromethanesulfonate

Product 1

HCID 21706791(E)-6-[2-(Phenyl)ethenyl]-2-naphthalenecarbonitrileYield 54%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 28B (350 mg, 1.16 mmol), styrene (157 mg, 1.51 mmol), palladium (II) acetate (26 mg, 0.12 mmol), triphenylphosphine (61 mg, 0.23 mmol), triethylamine (2 mL) and acetonitrile (1 mL) in a sealed tube with minimal head volume was heated at 100° C. for 19 h, diluted with ethyl acetate (20 mL), washed with water, dried (MgSO4) and concentrated with silica gel (4 g). The mixture was chromatographed on silica gel with 10% ethyl acetate/hexane to provide 160 mg of the title compound.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated with silica gel (4 g)
  4. customThe mixture was chromatographed on silica gel with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3a5835c1557c41ea882c670eadc15f85
Source dataset
uspto-grants-2001_07
Patent number
US06258822B1

Reaction notes

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