Methanol → 4-(3-Phenyl-1,2,4-oxadiazol-5-yl)benzoic acid

HRID 533713Notes

Reaction equation

HRID 533713 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=3)[O:10][N:9]=2)=[CH:4][CH:3]=1.CO.[Li+].[OH-]>C1COCC1.O>[C:5]1([C:8]2[N:12]=[C:11]([C:13]3[CH:14]=[CH:15][C:16]([C:17]([OH:19])=[O:18])=[CH:21][CH:22]=3)[O:10][N:9]=2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 6460108HCID 6460108, compound

Product 1

HCID 125192934-(3-Phenyl-1,2,4-oxadiazol-5-yl)benzoic acidYield 96.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(3-(4-fluorophenyl) 1,2,4-oxadiazol-5-yl)benzoate (600 mg, 2.14 mmol) in THF (12 mL) was added MeOH (3 mL) and a solution of LiOH (351 mg, 8.57 mmol) in H2O (3 mL). The reaction was stirred at room temperature for 2 h. The reaction was quenched upon the addition of 1N HCl (30 mL) and extracted with EtOAc (2×30 mL). The organic extracts were dried over MgSO4, and concentrated under vacuum to afford 4-(3-phenyl-1,2,4-oxadiazol-5-yl)benzoic acid (550 mg, 87%) as a white solid. 1H-nmr (400 MHz, CDCl3) δ 8.37 (d, J=8 Hz, 2H), 8.30 (d, J=8 Hz, 2H), 8.26-8.19 (m, 2H), 7.62-7.52 (m, 3H); MS (ESI) m/z 266.8

Workup

  1. customThe reaction was quenched upon the addition of 1N HCl (30 mL)
  2. extractionextracted with EtOAc (2×30 mL)
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7f42632428cf44909e29c82ff2bd72bc
Source dataset
uspto-grants-2014_10
Patent number
US08853392B2

Reaction notes

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