3-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-acrylonitrile → 3-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-propionitrile
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]#[N:21])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=1>CO.[Pd]>[OH:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][C:20]#[N:21])[C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)=[CH:7][C:6]=2[CH:17]=1Participants
4
Procedure
A solution of 3-[5-hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-acrylonitrile 64 (0.028 g, 0.1 mmol) in methanol (1 mL) was purged with nitrogen and 10% palladium on carbon added. The reaction vessel was evacuated and a hydrogen balloon added. After an hour, the reaction was filtered and the solvent removed in vacuo. The product was purified via flash chromatography, eluting with 3% methanol in dichloromethane to give 0.007 g of 3-[5-hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-propionitrile 65: 1H NMR (DMSO-d6) δ 9.84 (s, 1 H), 9.17 (s, 1 H), 7.73 (d, 2 H, J=8.6 Hz), 7.02 (s, 1 H), 6.87 (d, 2 H, J=8.6 Hz), 6.79 (d, 1 H, J=2.3 Hz), 6.62 (d, 1 H, J=2.2 Hz), 3.12 (t, 2 H, J=7.1 Hz), 2.96 (t, 2 H, J=7.4 Hz); MS 280 (M+H)+.