Sodium borohydride → (2-Methoxypyridin-3-yl)methanol

To a solution of 2-methoxy-pyridine-3-carbaldehyde (2.05 g, 14.9 mmol) in MeOH (70 mL) cooled to 0° C. was added sodium borohydride (670 mg, 17.7 mmol, 1.18 equiv.) as a solid in one portion. The reaction was allowed to slowly warm to room temperature and stirred for 2 h. Excess hydride was consumed by the addition of H2O and the reaction mixture was concentrated under reduced pressure. The residue was taken back up in EtOAc and washed with H2O. The aqueous phase was back extracted with EtOAc and the combine organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by flash silica gel chromatography using a 5% MeOH/DCM to provide, after concentration of the eluent, to give (2-methoxy-pyridin-3-yl)-methanol (1.65 g, 11.9 mmol, 81.3 %) as a white solid.

1. customExcess hydride was consumed by the addition of H2O
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. washwashed with H2O
4. extractionThe aqueous phase was back extracted with EtOAc
5. washthe combine organic phase was washed with brine
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe crude residue was purified by flash silica gel chromatography
9. customto provide

ORD record

ord-74a1152ecc664c61bf34f276ccd7439c

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601714B2