反応 #10825

反応方程式

2-cyclopropyl-4-(2,4-dimethoxy-phenyl)-1H-imidazole

dichloromethyl methyl ether

→

5-(2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxy-benzaldehyde

反応条件

後処理

1. 1
   workup.ADDITIONThe reaction mixture was then poured into ice
2. 2
   抽出extracted with dichloromethane
3. 3
   洗浄The combined solution of dichloromethane was washed with saturated solution of sodium bicarbonate, brine
4. 4
   乾燥dried over sodium sulfate
5. 5
   濃縮concentrated

実験手順

Ex-105B: To a solution of 2-cyclopropyl-4-(2,4-dimethoxy-phenyl)-1H-imidazole (0.51 g, 2.09 mmol) was added dichloromethyl methyl ether (0.28 mL, 3.13 mmol) followed by addition of titanium tetrachloride (1.0M in dichloromethane, 8.4 mL, 8.4 mmol) dropwise at 0° C. The solution was allowed to warm up to ambient temperature and stir for 4.5 hours. The reaction mixture was then poured into ice. The aqueous layer was adjusted to pH 12 and extracted with dichloromethane. The combined solution of dichloromethane was washed with saturated solution of sodium bicarbonate, brine, dried over sodium sulfate and concentrated to afford 5-(2-cyclopropyl-1H-imidazol-4-yl)-2,4-dimethoxy-benzaldehyde which was used without further purification. 1H NMR (DMSO-d6) δ 13.95 (bs, 1H), 10.22 (s, 1H), 8.09 (s, 1H), 7.70 (s, 1H), 6.88 (s, 1H), 4.04 (s, 3H), 4.00 (s, 3H), 2.25 (m, 1H), 1.20 (m, 4H). MS m/z=245 ([M+H]+, 100%).

出典