Acetaldehyde → HCID 57515866, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence