Pyridine → HCID 12458458, Verbindung

To a suspension of N-chlorosuccimide (71.5 g, 535 mmol) in CHCl3 (360 mL) and pyridine (1.61 g, 20.3 mmol) was added a solution of (E)-acetaldehyde oxime (31.6 g, 535 mmol). After a period of 1 h, propargylacetate (35.0 g, 357 mmol) in a minimum of CHCl3 was added to the previous mixture. Triethylamine (114 g, 1124 mmol) was then added dropwise and the reaction mixture was cooled in a water bath in order to maintain the internal temperature below the boiling point. After a period of 1 h, the reaction mixture was concentrated in vacuo followed by the addition of EtOAc. The mixture was filtered on a glass filter and the solid washed with EtOAc, the combined filtrates were evaporated. After evaporation, additional EtOAc was added and the previous process repeated. The EtOAc was evaporated and the crude product was purified on a on Biotage system (isocratic elution 40% EtOAc:60% Hexanes) and the fractions followed by LC/MS to provide the titled compound as a clear oil. LC/MS m/z 156 [M+H]+.

1. temperaturethe reaction mixture was cooled in a water bath in order
2. temperatureto maintain the internal temperature below the boiling point
3. waitAfter a period of 1 h
4. concentrationthe reaction mixture was concentrated in vacuo
5. additionfollowed by the addition of EtOAc
6. filtrationThe mixture was filtered on a glass
7. filtrationfilter
8. washthe solid washed with EtOAc
9. customthe combined filtrates were evaporated
10. customAfter evaporation, additional EtOAc
11. additionwas added
12. customThe EtOAc was evaporated
13. customthe crude product was purified on a
14. washon Biotage system (isocratic elution 40% EtOAc:60% Hexanes)

ORD-Eintrag

ord-619851051efa43d6bad1c85bae07f348

Quelldatensatz

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08796261B2