反应详情

温度

-78 °C

Methyl magnesium bromide (9.70 mL, 1.0 M tetrahydrofuran solution) was added dropwise to a tetrahydrofuran (4.0 mL) solution of 1-ethynyl-4-(trifluoromethyl)benzene (1.80 mL) under cooling in an ice bath, and the obtained solution was then stirred for 2 hours. Thereafter, the reaction solution was cooled to −78° C., and a tetrahydrofuran (6.2 mL) solution of N-methoxy-N,1-dimethyl-1H-pyrazol-5-carboxamide (867 mg) was then added thereto. The obtained mixture was stirred for 1 hour, and was then stirred for 2.5 hours under cooling in an ice bath. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1), so as to obtain the title compound (1.09 g) in the form of a yellow oily substance.

1. temperatureunder cooling in an ice bath
2. stirringThe obtained mixture was stirred for 1 hour
3. stirringwas then stirred for 2.5 hours
4. temperatureunder cooling in an ice bath
5. extractionthe obtained mixture was then extracted with ethyl acetate
6. washThe organic layer was washed with a saturated saline
7. dry with materialwas then dried over anhydrous magnesium sulfate
8. concentrationfollowed by vacuum concentration
9. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=9:1)