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

HRID 1020554Notes

Reaction equation

HRID 1020554 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-8be181e8647d484c933d8ffb8f3fe4b2
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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