Reaction #92151

Reaction equation

methyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]naphthalene-1-carboxylate

NaOH

→

4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]naphthalene-1-carboxylic acid

Solvents

methanol

Conditions

Workup

1. 1
   OtherInto a 50-mL round-bottom flask, was placed
2. 2
   TemperatureThe reaction mixture was cooled
3. 3
   ConcentrationThe resulting mixture was concentrated under vacuum
4. 4
   FiltrationThe solids were collected by filtration
5. 5
   Washwashed with 10 mL H2O
6. 6
   OtherThen the solid was dried under infrared light
7. 7
   OtherThis resulted in 150 mg (77%) of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]naphthalene-1-carboxylic acid as a white solid

Procedure

Into a 50-mL round-bottom flask, was placed methanol (20 mL), methyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]naphthalene-1-carboxylate (200 mg, 0.40 mmol, 1.00 equiv), 15% NaOH (5 mL). The resulting solution was stirred for 2 h at 70° C. in an oil bath. The reaction mixture was cooled. The resulting mixture was concentrated under vacuum. The solids were collected by filtration and washed with 10 mL H2O. Then the solid was dried under infrared light. This resulted in 150 mg (77%) of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]naphthalene-1-carboxylic acid as a white solid.

Source