Methanol → 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoic acid

Temperature

90 °C

Into a 500-mL round-bottom flask, was placed ethyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoate (7 g, 14.59 mmol, 1.00 equiv), methanol (100 mL), water (100 mL), sodium hydroxide (1.75 g, 43.75 mmol, 3.00 equiv). The resulting solution was stirred for 4 h at 90° C. in an oil bath. The resulting mixture was concentrated under vacuum. The resulting solution was extracted with 2×50 mL of ethyl acetate and the aqueous layers combined. The pH value of the solution was adjusted to 1-2 with hydrogen chloride aq. The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×50 mL of brine. The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 5.1 g (77%) of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid as a light yellow solid.

1. customInto a 500-mL round-bottom flask, was placed
2. concentrationThe resulting mixture was concentrated under vacuum
3. extractionThe resulting solution was extracted with 2×50 mL of ethyl acetate
4. extractionwas extracted with 3×50 mL of ethyl acetate
5. washThe resulting mixture was washed with 2×50 mL of brine
6. dry with materialThe mixture was dried over anhydrous sodium sulfate
7. filtrationThe solids were filtered out
8. concentrationThe resulting mixture was concentrated under vacuum
9. customThis resulted in 5.1 g (77%) of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylbenzoic acid as a light yellow solid

ORD record

ord-5983f96800d245ebae54942cab9ca093

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447084B2