Sodium borohydride → (5-Fluoropyridin-2-yl)methanol

A suspension of 5-fluoropicolinaldehyde (10.0 g, 79.94 mmol) in MeOH (160 mL) was treated with sodium borohydride (9.073 g, 239.8 mmol) in portions. The mixture was stirred at ambient temperature for 16 hours. The mixture was quenched with water, concentrated under reduced pressure, diluted with water and extracted with EtOAc. The combined organic extracts were dried (phase separator silicone treated filter paper), and concentrated under reduced pressure to give a clear oil, which was triturated with ether. The resulting solid was collected by filtration to afford (5-fluoropyridin-2-yl)methanol (10.15 g, 99% yield).

1. customThe mixture was quenched with water
2. concentrationconcentrated under reduced pressure
3. additiondiluted with water
4. extractionextracted with EtOAc
5. customThe combined organic extracts were dried
6. addition(phase separator silicone treated filter paper)
7. concentrationconcentrated under reduced pressure
8. customto give a clear oil, which
9. customwas triturated with ether
10. filtrationThe resulting solid was collected by filtration

ORD record

ord-0ae13b38200f44a191d054b114a70d11

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841455B2