Ammonium Chloride → 3-[3-Chloro-4-(1-hydroxyethyl)phenyl]-5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

In a solution of 1.4 g of 2-chloro-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]benzaldehyde in 50 mL of diethyl ether under nitrogen atmosphere, 6.6 mL of a solution (0.87 mol/L) of methyl magnesium bromide in tetrahydrofuran was added dropwise with stirring at room temperature. After the completion of the addition dropwise, the mixture was continued to stir under reflux with heating further for 30 minutes. After the completion of the reaction, 5 mL of ammonium chloride aqueous solution was added in the reaction mixture under cooling with ice and with stirring, the mixture was extracted with ethyl acetate (50 mL×1), the organic phase was washed with water (30 mL×2), and dehydrated with and dried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order, and then the solvent was distilled off under reduced pressure to obtain 1.5 g of the aimed product as pale yellow resinous substance.

1. additionAfter the completion of the addition dropwise
2. stirringto stir
3. temperatureunder reflux
4. temperaturewith heating further for 30 minutes
5. additionwas added in the reaction mixture
6. temperatureunder cooling with ice
7. stirringwith stirring
8. extractionthe mixture was extracted with ethyl acetate (50 mL×1)
9. washthe organic phase was washed with water (30 mL×2)
10. dry with materialdried over saturated sodium chloride aqueous solution and anhydrous magnesium sulfate in that order
11. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-631e057482514146b3c95293a312174e

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947715B2