Hydrochloric Acid → (2-Chloropyridin-4-yl)methanol

4-Carboxy-2-chloropyridine (78.7 g) is added slowly to a suspension of sodium borohydride (28.4 g) in tetrahydrofuran (750 ml) under nitrogen atmosphere, and thereto is added dropwise boron trifluoride-ether complex (123 ml). The mixture is reacted at room temperature for six hours. To the mixture is added a 6 M hydrochloric acid (960 ml), and the mixture is concentrated under reduced pressure to remove the solvent. The resultant is basified with sodium hydroxide, and extracted with chloroform. The chloroform layer is washed with a saturated aqueous sodium hydrogen carbonate solution, dried and concentrated under reduced pressure to remove the solvent to give 2-chloro-4-hydroxymethylpyridine (62.2 g).

1. additionis added dropwise boron trifluoride-ether complex (123 ml)
2. customThe mixture is reacted at room temperature for six hours
3. concentrationthe mixture is concentrated under reduced pressure
4. customto remove the solvent
5. extractionextracted with chloroform
6. washThe chloroform layer is washed with a saturated aqueous sodium hydrogen carbonate solution
7. customdried
8. concentrationconcentrated under reduced pressure
9. customto remove the solvent

ORD record

ord-12a98202512f4a5f92246622e82e7efc

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05969140