(E)-2-Methoxy-4-styrylpyridine → 2-Methoxy-4-phenethylpyridine

HRID 930639Notes

Reaction equation

HRID 930639 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][N:4]=1>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 1

HCID 57950306(E)-2-Methoxy-4-styrylpyridine

Product 1

HCID 579504422-Methoxy-4-phenethylpyridineYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-2-Methoxy-4-styrylpyridine (22.15 g, 104.8 mmol) was dissolved in MeOH (400 mL) and degassed with a nitrogen stream for 10 minutes. Palladium on charcoal (10%, wet, 5 g) was added and the reaction mixture was stirred under an atmosphere of hydrogen for 24 h. The reaction mixture was degassed again, and the catalyst was removed by filtration. Concentration of the filtrate provided the title compound (22 g, 98%) as a green oil: 1H NMR (500 MHz, CDCl3) δ 8.04 (d, J=5.3 Hz, 1H), 7.29-7.24 (m, 2H), 7.21-7.15 (m, 3H), 6.69-6.67 (m, 1H), 6.54 (s, 1H), 3.91 (s, 3H), 2.91-2.89 (m, 2H), 2.87-2.84 (m, 2H).

Workup

  1. customdegassed with a nitrogen stream for 10 minutes
  2. additionPalladium on charcoal (10%, wet, 5 g) was added
  3. customThe reaction mixture was degassed again
  4. customthe catalyst was removed by filtration

Sources & evidence

ORD record
ord-2edc686ff41844caa058276c196e85cb
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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