EThyl (2E)-3-(2,6-dichloropyridin-3-yl)prop-2-enoate → Ethyl 3-(2,6-dichloropyridin-3-yl)propanoate
Reaction equation
[Cl:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=[C:4]([Cl:15])[N:3]=1>C(O)C.[Pt]>[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=[C:4]([Cl:15])[N:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (E)-ethyl 3-(2,6-dichloropyridin-3-yl)acrylate (500 mg, 2.032 mmol) in Ethanol (15 mL) was added 10% platinum on carbon (96 mg, 0.049 mmol). The flask was alternately evacuated and filled with hydrogen five times. The solution was stirred under 1 ATM (balloon) of hydrogen for 1 h, then filtered through celite, while washing well with MeOH and EtOAc. The filtrate was concentrated in vacuo to provide the title compound which was used without further purification. 1H NMR δ (ppm) (CHCl3-d): 7.62 (1H, d, J=7.92 Hz), 7.24 (1H, d, J=7.8), 4.15 (2H, q, J=7.15 Hz), 3.05 (2H, t, J=7.35 Hz), 2.69 (2H, t, J=7.35 Hz), 1.31˜1.24 (3H, m). MS (M+H)+: 247.