Acrolein → HCID 59780172, compound

Participants

Reaction Conditions

Reaction Steps

At −50° C., 3.45 g (12.4 mmol) of ethyl [(1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]acetate dissolved in THF were added dropwise to 18.5 ml (37.0 mmol) of a 2M solution of lithium diisopropylamide in THF/heptanelethylbenzene. After 1.5 h of stirring at −50° C., the mixture was cooled to −78° C. and 0.83 g (14.8 mmol) of acrolein dissolved in THF were added dropwise. After 2 h of stirring at −78° C., the mixture was hydrolyzed with sat. NH4Cl solution and warmed to RT. After separation of the phases, the organic phase was dried and the solvent was removed. The residue was purified chromatographically (SiO2, cyclohexane/ethyl acetate). This gave 1.65 g (40% of theory) of the title compound as a colorless solid (about 1:1 diastereomer mixture) which was used without further purification.

Provenance & Evidence