(E)-2-Methoxy-4-(2-(pyridin-2-yl)vinyl)pyridine → 2-Methoxy-4-(2-(pyridin-2-yl)ethyl)pyridine
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][N: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][N:12]=2)[CH:6]=[CH:5][N:4]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
(E)-2-Methoxy-4-(2-(pyridin-2-yl)vinyl)pyridine (290 mg, 0.13 mmol) was dissolved in MeOH (15 mL) and degassed with a nitrogen stream for 10 minutes. Palladium on charcoal (10%, wet, 5 g) was added and the reaction mixture stirred under an atmosphere of hydrogen for 24 h. The reaction mixture was degassed again and the catalyst removed by filtration. Concentration of the filtrate provided the title compound (200 mg, 90%) as a green oil: 1H NMR (500 MHz, CD3OD) δ 8.56 (d, J=5.1 Hz, 1H), 8.03 (d, J=5.1 Hz, 1H), 7.59-7.55 (dt, J=7.9, 19 Hz, 1H), 7.14-7.10 (dd, J=7.2, 5.1 Hz, 1H), 7.08 (d, J=7.6 Hz, 1H), 6.71 (d, J=5.4 Hz, 1H), 6.56 (s, 1H), 3.90 (s, 3H), 3.10-3.06 (m, 2H), 3.04-3.00 (m, 2H).