Methyl 3-(3-cyanophenyl)prop-2-enoate → Methyl 3-(3-cyanophenyl)propanoate
Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=1>[Pd].CCOC(C)=O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of 3-(3-cyano-phenyl)-acrylic acid methyl ester (3.24 g, 17.31 mmol), prepared in Step B of Preparation 44, and palladium on carbon (10%, 0.600 g) in EtOAc (30 mL) was hydrogenated at 25 psi in a Parr shaker for 1 h. The catalyst was removed via filtration through Celite and the solution was concentrated in vacuo. Medium pressure chromatography (6:1 hexanes:EtOAc) provided the title compound of Step A as a clear oil (2.98 g). 1H NMR (400 MHz, CDCl3) δ 7.50-7.36 (m, 4H), 3.65 (s, 3H), 2.97 (t, 2H), 2.63 (t, 2H); MS 190 (M+1).