Acrolein → Ethyl 3-hydroxy-2-(4-fluoro-2-trifluoromethylbenzoylamino)pent-4-enoate

Participants

Reaction Conditions

Reaction Steps

At −78° C., 6.0 g (0.0205 mol) of ethyl (4-fluoro-2-trifluoromethylbenzoylamino)acetate dissolved in THF were added dropwise to 24.3 ml (0.049 mol) of a 2M lithium diisopropylamide solution in THF. After 1 h at −78° C., 1.4 g (0.025 mol) of acrolein dissolved in THF were added dropwise, and the mixture was stirred at −78° C. for 1 h. Saturated NH4Cl solution was then added, and the mixture was allowed to warm to RT. The mixture was extracted with CH2Cl2, and the combined organic phases were then washed and dried and the solvent was removed. The residue was purified chromatographically (SiO2; cyclohexane/ethyl acetate). This gave 4.7 g (66% of theory) of the title compound as a colorless solid (diastereomer mixture) which was reacted further without further purification.

Provenance & Evidence