Sodium cyanoborohydride → (5-(Phenylethynyl)pyridin-3-yl)methanol
Reaction equation
C([BH3-])#N.[Na+].[C:5]1([C:11]#[C:12][C:13]2[CH:14]=[C:15]([CH:19]=[O:20])[CH:16]=[N:17][CH:18]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OCC)(=O)C>[C:5]1([C:11]#[C:12][C:13]2[CH:14]=[C:15]([CH2:19][OH:20])[CH:16]=[N:17][CH:18]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Add sodium cyanoborohydride (0.31 g, 4.98 mmol) to a solution of 5-phenylethynyl-pyridine-3-carbaldehyde, (prepared as described in EXAMPLE 5), (0.86 g, 4.15 mmol) and stir at room temperature for 2 h. Dilute with ethyl acetate, wash with an aqueous saturated solution of bicarbonate, dry (magnesium sulfate), filter and concentrate. Purify by silica gel chromatography, eluting with 0:100 to 50:50 ethyl acetate:hexanes, to give the title compound as a colorless oil which solidifies on standing (0.465 g, 53%).