Sodium borohydride → 1-[6-(4-Benzotriazol-2-yl-but-1-ynyl)-pyridin-2-yl]-ethanol
Reaction equation
[BH4-].[Na+].[N:3]1[N:4]([CH2:12][CH2:13][C:14]#[C:15][C:16]2[N:21]=[C:20]([C:22](=[O:24])[CH3:23])[CH:19]=[CH:18][CH:17]=2)[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12>CO>[N:3]1[N:4]([CH2:12][CH2:13][C:14]#[C:15][C:16]2[N:21]=[C:20]([CH:22]([OH:24])[CH3:23])[CH:19]=[CH:18][CH:17]=2)[N:5]=[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
NaBH4 (99 mg, 1.6 mmol) was added to a solution of 1-[6-(4-benzotriazol-2-yl-but-1-ynyl)-pyridin-2-yl-]-ethanone (380 mg, 1.31 mmol) in MeOH (5 mL) at 0° C. The reaction mixture was stirred at room temperature for 30 min., quenched by the addition of water at 0° C. and extracted twice with DCM. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 3:2) to yield 202 mg (0.69 mmol, 53%) of 1-[6-(4-benzotriazol-2-yl-but-1-ynyl)-pyridin-2-yl]-ethanol as a colorless oil.