2,4-Dimethoxybenzaldehyde → N-(2,4-dimethoxybenzyl)prop-2-yn-1-amine

反応式

[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH2:13]([NH2:16])[C:14]#[CH:15].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:16][CH2:13][C:14]#[CH:15]

参加物

実験手順

To a solution of 2,4-dimethoxybenzaldehyde (2.51 g, 15.13 mmol) in methanol (100 ml) was added prop-2-yn-1-amine (1.0 g, 18.16 mmol). The reaction mixture was stirred at room temperature for 1.5 hours, and cooled to 0° C. NaBH4 (1.0 g, 27.2 mmol) was added in portions over 15 minutes. The mixture was warmed up to room temperature and stirred for additional 2 hours. The reaction mixture was quenched with brine (200 mL), and partitioned between brine and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over MgSO4, filtered, and concentrated to afford the title compound. MS (DCI/NH3) m/z 206 (M+H)+.