Sodium borohydride → (6-Methoxypyridin-2-yl)methanol

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Reaction Steps

To 6-methoxy-pyridine-2-carbaldehyde (J. Org. Chem. 1990, 55, 69-73) (11.0 g, 80.3 mmol) in wet THF (200 mL) add portion wise with stirring sodium borohydride (3.0 g, 79 mmol) and continue stirring for 1 h at ambient temperature. Add brine, extract the reaction mixture twice with EtOAc, dry the organic layer over anhydrous Na2SO4 and concentrate in vacuo. Pass the residue through a small plug of silica gel eluting with hexane/EtOAc (3:1) to provide the desired intermediate as a clear liquid (9.0 g, 81%).

Provenance & Evidence