Ammonium Chloride → HCID 23120650, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4.00 g of tert-butyl[4-chloro-3-(trifluoromethyl)phenyl]carbamate in Et2O (30 ml) under cooling at −78° C. was added dropwise a solution of 1.6 mol/L tert-butyl lithium in n-pentane (21 ml), and the reaction mixture was stirred for 1 hour. Thereafter, the solution was warmed to −40° C. and was stirred under the same temperature condition for 2.5 hours. The solution was cooled again to −78° C., a solution of 4.25 g of ethyl oxo[2-(trifluoromethoxy)phenyl]acetate in THF (15 ml) was added dropwise to the reaction mixture and the reaction mixture was stirred under the same temperature condition for two hours. Thereafter, the solution was warmed to room temperature and stirred for 15 hours. To the reaction solution was added a saturated aqueous solution of NH4Cl, the resulting mixture was extracted with EtOAc, the organic layer was washed with saturated brine, dried over MgSO4 and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silicagel 60; mobile phase: EtOAc/n-hexane=1/4; v/v) to obtain 3.57 g of the title compound (colorless powder).

Provenance & Evidence