1-Butanol → 5-Bromo-2-butoxypyridine

반응식

[H-].[Na+].[H][H].Br[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][N:7]=1.[CH2:13]([OH:17])[CH2:14][CH2:15][CH3:16]>>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([O:17][CH2:13][CH2:14][CH2:15][CH3:16])=[N:7][CH:8]=1

참가 물질

반응물 4

HCID 2631-Butanol

HCID 24758Sodium hydride

HCID 693532,5-Dibromopyridine

HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 189362685-Bromo-2-butoxypyridine

실험 절차

Sodium hydride (60% w/v dispersion in mineral oil; 1.8 g) was added in portions over 20 minutes to n-butanol (100 ml) with stirring. The mixture was then stirred until no further hydrogen evolution was noted. 2,5-Dibromopyridine (7.1 g) was added and the resulting mixture stirred at reflux for 6 hours. After cooling, the n-butanal was removed by evaporation and the residue was treated with water (50 ml) and extracted with dichloromethane (2×20 ml). The organic extracts were combined, washed with water (20 ml), dried (MgSO4) and evaporated to give 5-bromo-2-n-butoxypyridine (6.3) as a pale yellow oil, NMR (DHSOd6): 0.9-0.96(3H, t), 1.32-1.5(2H, m), 1.62-1.76(2H, m), 4.2-4.28(2H, t), 6.79-6.82(1H, d), 7.85-7.9(1H, d of d) and 8.26(1H, d).