4-Vinylpyridine → 4-(2-Phenylvinyl)pyridine, trans-

HRID 343348Notes

Reaction equation

HRID 343348 reaction equation
[C:1]1(I)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:8]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)=[CH2:9].C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:1]1(/[CH:9]=[CH:8]/[C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 11575Iodobenzene

Product 1

HCID 6410984-(2-Phenylvinyl)pyridine, trans-Yield 56%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of phenyl iodide (100 ml, 0.89mol), 4-vinylpyridine (115 ml, 1.07 mol), palladium acetate (2.4 g, 0.01 mol), tri-o-tolylphosphine (6.08 g, 0.02 mol) and triethylamine (150 ml, 1.07 mol) was refluxed for 3 hours. The reaction was cooled to room temperature, the resulting solid dissolved in dichloromethane (2 l) and washed with saturated aqueous sodium carbonate solution (2 l). The aqueous phase was further extracted with dichloromethane (3×1.5 l) and the combined organic phases dried (MgSO4) and evaporated. The resulting solid was washed with ethyl acetate (1.5 l), filtered and dried in vacuo to give (E)-4-(2-phenylethenyl)pyridine (90 g, 56%); δH (CDCl3) 7.01 (1H, d, J 16.3 Hz, ArCH=CH), 7.25-7.41 (6H, m, PhH, ArCH=CH), 7.53 (2H, d, J 5.3 Hz, 3-H, 5-H), and 8.58 (2H, d, J 5.2 Hz, 2-H, 6-H).

Workup

  1. temperaturewas refluxed for 3 hours
  2. washwashed with saturated aqueous sodium carbonate solution (2 l)
  3. extractionThe aqueous phase was further extracted with dichloromethane (3×1.5 l)
  4. dry with materialthe combined organic phases dried (MgSO4)
  5. customevaporated
  6. washThe resulting solid was washed with ethyl acetate (1.5 l)
  7. filtrationfiltered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-b5ab125244474181a30093893a9c3571
Source dataset
uspto-grants-1999_01
Patent number
US05861407

Reaction notes

Loading…