Sodium borohydride → 4-Methoxy-3-pyridinemethanol

To a solution of 4-methoxy-pyridine-3-carbaldehyde (2.1 g, 14.9 mmol) in MeOH (70 mL) cooled to 0° C. was added sodium borohydride (0.67 g, 17.7 mmol) 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 water and the reaction mixture was concentrated under reduced pressure. The residue was taken back up in EtOAc and washed with water. The aqueous phase was back extracted with EtOAc and the combined 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 95:5 CH2Cl2:MeOH as an eluent to provide, after concentration, to give 1.1 g (55%) of (4-methoxy-pyridin-3-yl)-methanol as a white solid.

1. customExcess hydride was consumed by the addition of water
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. washwashed with water
4. extractionThe aqueous phase was back extracted with EtOAc
5. washthe combined 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. customMeOH as an eluent to provide
10. concentrationafter concentration

ORD record

ord-eaa789cd92194d148459d99c382fc134

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601714B2