Water → Methyl 4-(5-phenyl-3-isoxazolyl)benzoate

HRID 1354432Notes

Reaction equation

HRID 1354432 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][CH:20]=[CH:19][CH:18]=1)#[CH:16].C(N(CC)CC)C.O>O1CCCC1>[C:17]1([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][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 73989494alpha-Chloro-4-methoxycarbonylbenzaldoxime

Product 1

HCID 22934529Methyl 4-(5-phenyl-3-isoxazolyl)benzoateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution (70 ml) of methyl 4-[chloro(hydroxyimino)methyl]benzoate (2.20 g) and ethynylbenzene (1.3 ml) in tetrahydrofuran was added dropwise a solution (10 ml) of triethylamine (3.0 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-tetrahydrofuran to give methyl 4-(5-phenyl-3-isoxazolyl)benzoate (2.47 g, yield 86%) as colorless crystals. melting point: 201–202° 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-tetrahydrofuran

Sources & evidence

ORD record
ord-1566b70a83f84e9483a423477f081d4b
Source dataset
uspto-grants-2007_05
Patent number
US07223791B2

Reaction notes

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