N,N-Diethyl-2,2,2-trifluoroacetamide → HCID 68071560, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 1-(4-bromophenyl)ethylcarbamate (6.35 g, 21.2 mmol) was dissolved in dry THF (100 ml) and cooled to −78° C. under an atmosphere of nitrogen. n-Butyllithium (21 ml, 52.9 mmol, 2.5M in hexanes) was added dropwise under 10 minutes and the reaction was stirred at −78° C. for 3 hours. A solution of diethyl trifluoroacetamide (5.0 g, 29.6 mmol) in 10 ml dry THF was added dropwise and the reaction was stirred 1.5 hours at −78° C. Reaction was quenched with NH4Cl (sat) (50 ml) and H2O (50 ml) and allowed to reach room temperature. The aqueous phase was separated and extracted with EtOAc (100 ml). The combined organics were washed with NH4Cl (sat) (2*100 ml), H2O (100 ml), dried over MgSO4, filtered and evaporated. Unreacted starting material was removed by precipitation from MeOH/H2O (9/1). The mother liquor was evaporated and the residue purified by flash chromatography using Pet. Ether/EtOAc (7:1→5:1) as eluent to give 3.09 g (46%) of the title compound as white solids.

Provenance & Evidence