Water → Methyl 4-[5-(4-trifluoromethylphenyl)-3-isoxazolyl]benzoate

HRID 1354441Notes

Reaction equation

HRID 1354441 reaction equation
Cl[C:2](=[N:13][OH:14])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)#[CH:16].C(N(CC)CC)C.O>O1CCCC1>[F:24][C:23]([F:25])([F:26])[C:20]1[CH:19]=[CH:18][C:17]([C:15]2[O:14][N:13]=[C:2]([C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=3)[CH:16]=2)=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 43482951-Ethynyl-4-(trifluoromethyl)benzeneHCID 73989494alpha-Chloro-4-methoxycarbonylbenzaldoxime

Product 1

HCID 15453642Methyl 4-[5-(4-trifluoromethylphenyl)-3-isoxazolyl]benzoateYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (15 ml) of methyl 4-[chloro(hydroxyimino)methyl]benzoate (0.425 g) and 1-ethynyl-4-trifluoromethylbenzene (0.534 g) in tetrahydrofuran was added dropwise a solution (10 ml) of triethylamine (0.697 ml) in tetrahydrofuran under an argon atmosphere at 0° C. This mixture was stirred overnight at room temperature and poured into water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from hexane-ethyl acetate to give methyl 4-[5-(4-trifluoromethylphenyl)-3-isoxazolyl]benzoate (0.563 g, yield 65%) as colorless needle crystals. melting point: 183–184° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-61ef69748e894fc6b28c512c8e0395ad
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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