Ethyl Acetate → HCID 67058165, compound

Temperature

-78 °C

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%).

1. additionwas added
2. stirringat −78° C., and the resulting mixture was stirred under a nitrogen atmosphere at −78° C. for 2 hours
3. extractionthe organic matter was extracted with ethyl acetate
4. washThe organic layer was washed with water
5. dry with materiala saturated sodium chloride solution, then dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
8. customwas obtained
9. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 30:70 (v/v)), whereby the objective title compound

ORD record

ord-e5b80ce0a04c4517adaec89ca6c3de67

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222281B2