Acetaldehyde → HCID 57515866, compound

Temperature

-78 °C

To a stirred solution of piperidine, 2,2,6,6-tetramethyl—(9.2 ml, 54 mmol) in THF (400 ml) at −78° C. was added butyllithium (−2.5 m in toluene; 18 ml, 45 mmol) dropwise. The reaction was then stirred at 0° C. for 5 min at −78° C., and a solution of 5-(methoxymethoxy)-2-(trifluoromethyl)pyridine (7.5 g, 36 mmol) in THF (100 ml) was added dropwise. The mixture was stirred for an additional 10 min, then acetaldehyde (20 ml, 362 mmol) was added and stirring continued for 15 min. the reaction was slowly quenched with H2O, warmed to RT, extracted with EtOAc (3×), combine organic layers were dried over MgSO4, filtered, concentrated and the crude product was purified by ISCO (20% EtOAc/Hexanes) to give the title compound as a light yellow solid. MS (m+1): 252.2.

1. stirringThe mixture was stirred for an additional 10 min
2. stirringstirring
3. waitcontinued for 15 min.
4. customthe reaction was slowly quenched with H2O
5. temperaturewarmed to RT
6. extractionextracted with EtOAc (3×)
7. dry with materialwere dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customthe crude product was purified by ISCO (20% EtOAc/Hexanes)

ORD record

ord-2b98b88953cf405bb4470052a06a00ca

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552181B2