Sodium Hydroxide → 4-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]naphthalene-1-carboxylic acid

HRID 63873Notes

Reaction equation

HRID 63873 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:31]([F:34])([F:33])[F:32])[O:16][N:15]=[C:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([C:27]([O:29]C)=[O:28])=[CH:19][CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2([C:31]([F:32])([F:33])[F:34])[O:16][N:15]=[C:14]([C:17]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]([C:27]([OH:29])=[O:28])=[CH:19][CH:18]=3)[CH2:13]2)[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86649802Methyl 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylate

Product 1

HCID 874343954-[5-[3-Chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]naphthalene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

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.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. temperatureThe reaction mixture was cooled
  3. concentrationThe resulting mixture was concentrated under vacuum
  4. filtrationThe solids were collected by filtration
  5. washwashed with 10 mL H2O
  6. customThen the solid was dried under infrared light
  7. customThis 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

Sources & evidence

ORD record
ord-44bc26eba1ad4c908dc5efbc02e391ac
Source dataset
uspto-grants-2016_09
Patent number
US09447084B2

Reaction notes

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