Ethyl Acetoacetate → HCID 15748275, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of hexane washed NaH (0.77 g, 19.1 mmoles) in 30 mL THF at 0° C. under a nitrogen atmosphere, was added dropwise a solution of ethyl acetoacetate (2.27 mL, 17.9 mmoles) in 30 mL THF. The mixture was stirred for 15 minutes before a 2.2 M solution of n-BuLi (8.2 mL, 17.9 mmoles) in THF was added dropwise via syringe. The resulting orange solution was stirred at 0° C. for 15 minutes and then cooled to -7S° C. A solution of trans-3-[5-(4-fluorophenyl)-3-(l-methylethyl)-1-(2-quinolinyl)-1H-pyrazol-4-yl]-2-propenal (4.61 g, 12.0 mmoles) in 50 mL THF was added dropwise and after 2 hours at -78° C. the reaction was quenched by adding 6 mL glacial HOAc and removing the cooling bath. The reaction was partitioned between 5% K2CO3 and Et2O. The organic layer was dried over MgSO4, filtered, and evaporated to give an orange oil. Chromatography (SiO2, 20% EtOAc/hexanes) gave 5.57 g (90%) of the title compound as a yellow solid, mp 47°-53° C.

Provenance & Evidence