Butanal → N-butyl-4-(4-fluorophenoxy)aniline

반응식

[F:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH:16](=O)[CH2:17][CH2:18][CH3:19].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[CH2:16]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:8][CH:9]=1)[CH2:17][CH2:18][CH3:19]

참가 물질

실험 절차

To a solution of 4-(4-fluorophenoxy)aniline (Apollo, 500 mg, 2.46 mmol) and butyraldehyde (240 μL, 2.71 mmol) in DCE (5.0 mL) were added 4 Å molecular sieves. The resulting reaction mixture was stirred at room temperature for 1 h. Next, Na(OAc)3BH (782 mg, 3.69 mmol) was added, and the reaction mixture was stirred at room temperature overnight. Concentration in vacuo afforded a crude residue which was purified by flash column chromatography (10% EtOAc/hexanes) to give the title compound (400 mg, 62%). 1H NMR (CDCl3) δ 7.28-7.21 (m, 2H), 7.20-7.13 (m, 4H), 6.91-6.85 (m, 2H), 3.82 (br s, 1H), 3.39 (t, J=7.0 Hz, 2H), 1.96-1.85 (m, 2H), 1.79-1.67 (m, 2H), 1.26 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 260.1 (M+H)+.