Trifluoroacetic anhydride → 4-Chloro-2-methyl-1-oxo-1lambda~5~-pyridine

Temperature

0 °C

4-Chloro-2-methylpyridine (5.0 g, 39 mmol, 1.0 eq) and hydrogen peroxide-urea adduct (7.37 g, 78.4 mmol, 2.00 eq) were dissolved in THF (196 mL) and cooled to 0° C. Trifluoroacetic anhydride (12 mL, 86.3 mmol, 2.2 eq) was added dropwise over 15 minutes and the reaction was allowed to warm to room temperature. After determination of the completion of the reaction by LCMS (approximately 45 minutes), the reaction was cooled to 0° C. and quenched with a 10% aqueous solution of NaS2O3. The reaction was extracted with EtOAc (3×), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 5.63 g (99%) of the title compound as a white solid.

1. temperatureto warm to room temperature
2. customAfter determination of the completion of the reaction by LCMS (approximately 45 minutes)
3. temperaturethe reaction was cooled to 0° C.
4. customquenched with a 10% aqueous solution of NaS2O3
5. extractionThe reaction was extracted with EtOAc (3×)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification by flash chromatography on silica gel

ORD record

ord-6889921f59a74fdeb0cb834e3fdebee7

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09085562B2