Sodium borohydride → 1-(5-Bromopyridin-2-yl)ethanol
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:10])[CH3:9])=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-(5-bromopyridin-2-yl)ethanone (1.1 g, 5.5 mmol) in ethanol (100 mL) was added sodium borohydride (2.5 g, 66.1 mmol). The reaction mixture was stirred at room temperature for 24 hours. The mixture was filtered, the filtrate was acidified and the solvent removed on a rotary evaporator. The residue was taken up with water (50 mL) and extracted with dichloromethane (50 mL). The combined extract was dried over sodium sulfate, filtered, concentrated and purified by column chromatography to give 1-(5-bromopyridin-2-yl)ethanol (1.0 g, 90.0%) as a yellow oil. LRMS (M+H+) m/z: calcd 201.98. found 202. 1H NMR (300 MHz, CD3OD) δ 8.54 (d, J=2.4 Hz, 1H), 7.98 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 4.85 (m, 1H), 1.45 (d, J=6.6 Hz, 3H).