Sodium Hydroxide → HCID 90389322, compound

To a solution of 5-chloro-3-(fluoromethyl)picolinaldehyde (55 mg, 0.32 mmol) in THF (2 mL) and water (4 mL) was added solid NaOH (13 mg) at 0° C. After 10 min, KMNO4 (100 mg) was added in one portion. After additional 10 min, the reaction mixture was filtered through a pad of celite. The celite was washed with 1 M HCl (10 mL), water and EtOAc. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over MgSO4 and the filtrate was concentrated under reduced pressure. The title compound was obtained as a yellow residue and taken onto the next step without further purification. LC/MS m/z=172.1 [M+H]+.

1. additionKMNO4 (100 mg) was added in one portion
2. waitAfter additional 10 min
3. filtrationthe reaction mixture was filtered through a pad of celite
4. washThe celite was washed with 1 M HCl (10 mL), water and EtOAc
5. customThe phases were separated
6. extractionthe aqueous phase was extracted with EtOAc
7. dry with materialThe combined organic layers were dried over MgSO4
8. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-c927a4e6fe1244f9b731e8951f12d662

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085576B2