Sodium cyanoborohydride → (5-(Phenylethynyl)pyridin-3-yl)methanol

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Reaction Steps

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%).

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