反応 #80822

反応方程式

hydrogen

hydrogen

2-Acetylquinoline

→

2-(1-hydroxyethyl)tetrahydroquinoline

収率 78.0%

溶媒

acetic acid

反応条件

後処理

1. 1
   その他was consumed
2. 2
   濃縮concentrated
3. 3
   その他The residue was purified by column chromatography with 5:1 to 1:1 hexane/ethyl acetate

実験手順

2-Acetylquinoline (21.0 g, 0.123 mol) in acetic acid (210 mL) was hydrogenated over platinum oxide (1.0 g) under atmospheric pressure of hydrogen at room temperature until the theoretical amount of hydrogen was consumed. The mixture was passed through celite and concentrated. The residue was purified by column chromatography with 5:1 to 1:1 hexane/ethyl acetate to give 16.85 g of 2-(1-hydroxyethyl)tetrahydroquinoline (78%): 1H NMR (270 MHz, CDCl3) δ6.95 (m, 2H), 6.62 (td, 1H, J=7.3, 1 Hz), 6.51 (dd, 1H, J=7.3, 1 Hz), 3.81 (dq, 1H, J=10.2, 6.6 Hz), 1.87 (m, 1H), 1.76 (m, 1H), 1.20 (d, 3H, J=6.6 Hz).

出典