ethyl 2-oxo-2-[2-(trifluoromethoxy)phenyl]acetate

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 21 mL of a heptane solution of 1.6 mol/L tert-butyllithium was added dropwise under −78° C. cooling to a 30 mL diethyl ether solution of 4.00 g of tert-butyl[4-chloro-3-(trifluoromethyl)phenyl]carbamate, and the reaction mixture was stirred for 1 hour. The temperature was then raised to −40° C., and the reaction mixture was stirred for 2.5 hours at that temperature. The reaction mixture was cooled back down to −78° C., a 15 mL tetrahydrofuran solution of 4.25 g of ethyl oxo[2-(trifluoromethoxy)phenyl]acetate was added dropwise, and the reaction mixture was stirred for 2 hours at the same temperature. The temperature was then raised to room temperature, and the reaction mixture was stirred for 15 hours. A saturated ammonium chloride aqueous solution was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was washed with saturated brine and dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane=1/4; v/v) to obtain 3.57 g of the titled compound (colorless powder). the reaction mixture was stirred for 2.5 hours at that temperature The reaction mixture was cooled back down to −78° C. the reaction mixture was stirred for 2 hours at the same temperature The temperature was then raised to room temperature the reaction mixture was stirred for 15 hours the organic layer was washed with saturated brine dried with magnesium sulfate the solvent was distilled off under reduced pressure The residue was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane=1/4; v/v)

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 21 mL of a heptane solution of 1.6 mol/L tert-butyllithium was added dropwise under −78° C. cooling to a 30 mL diethyl ether solution of 4.00 g of tert-butyl[4-chloro-3-(trifluoromethyl)phenyl]carbamate, and the reaction mixture was stirred for 1 hour. The temperature was then raised to −40° C., and the reaction mixture was stirred for 2.5 hours at that temperature. The reaction mixture was cooled back down to −78° C., a 15 mL tetrahydrofuran solution of 4.25 g of ethyl oxo[2-(trifluoromethoxy)phenyl]acetate was added dropwise, and the reaction mixture was stirred for 2 hours at the same temperature. The temperature was then raised to room temperature, and the reaction mixture was stirred for 15 hours. A saturated ammonium chloride aqueous solution was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was washed with saturated brine and dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane=1/4; v/v) to obtain 3.57 g of the titled compound (colorless powder). the reaction mixture was stirred for 2.5 hours at that temperature The reaction mixture was cooled back down to −78° C. the reaction mixture was stirred for 2 hours at the same temperature The temperature was then raised to room temperature the reaction mixture was stirred for 15 hours the organic layer was washed with saturated brine dried with magnesium sulfate the solvent was distilled off under reduced pressure The residue was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane=1/4; v/v)

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). was stirred under the same temperature condition for 2.5 hours The solution was cooled again to −78° C. the reaction mixture was stirred under the same temperature condition for two hours Thereafter, the solution was warmed to room temperature stirred for 15 hours the resulting mixture was extracted with EtOAc the organic layer was washed with saturated brine dried over MgSO4 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)

Conditions: temp:-40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 21 mL of a heptane solution of 1.6 mol/L tert-butyllithium was added dropwise under −78° C. cooling to a 30 mL diethyl ether solution of 4.00 g of tert-butyl[4-chloro-3-(trifluoromethyl)phenyl]carbamate, and the reaction mixture was stirred for 1 hour. The temperature was then raised to −40° C., and the reaction mixture was stirred for 2.5 hours at that temperature. The reaction mixture was cooled back down to −78° C., a 15 mL tetrahydrofuran solution of 4.25 g of ethyl oxo[2-(trifluoromethoxy)phenyl]acetate was added dropwise, and the reaction mixture was stirred for 2 hours at the same temperature. The temperature was then raised to room temperature, and the reaction mixture was stirred for 15 hours. A saturated ammonium chloride aqueous solution was added to the reaction solution, extraction was performed with ethyl acetate, the organic layer was washed with saturated brine and dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane=1/4; v/v) to obtain 3.57 g of the titled compound (colorless powder). the reaction mixture was stirred for 2.5 hours at that temperature The reaction mixture was cooled back down to −78° C. the reaction mixture was stirred for 2 hours at the same temperature The temperature was then raised to room temperature the reaction mixture was stirred for 15 hours the organic layer was washed with saturated brine dried with magnesium sulfate the solvent was distilled off under reduced pressure The residue was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/hexane=1/4; v/v)