Ethyl Acetate → HCID 67058165, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl acetate (0.255 mL, 2.57 mmol) was dissolved in tetrahydrofuran (10 mL), and a 1 M lithium bis(trimethylsilyl)amide hexane solution (2.57 mL, 2.57 mmol) was added thereto at −78° C., and then, the resulting mixture was stirred under a nitrogen atmosphere at −78° C. for 1 hour. Thereafter, a tetrahydrofuran solution of 4-{[8-(trifluoromethyl)quinolin-4-yl]oxy}benzaldehyde (680 mg, 2.14 mmol) synthesized in (22A) was added thereto at −78° C., and the resulting mixture was stirred under a nitrogen atmosphere at −78° C. for 2 hours. To the reaction solution, a saturated aqueous solution of ammonium chloride was added at −78° C., and the organic matter was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 30:70 (v/v)), whereby the objective title compound was obtained as a white solid (730 mg, yield: 84%).

Provenance & Evidence