Sulfuric Acid → 5-Isoxazoleacetic acid, 3,4-bis(4-methoxyphenyl)-, methyl ester

HRID 1033532Notes

Reaction equation

HRID 1033532 reaction equation
[OH:1][N:2]=[C:3]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:4]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[CH:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].S(=O)(=O)(O)O>C(O)(=O)C.O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[CH3:10][O:9][C:7]([CH2:6][C:5]1[O:1][N:2]=[C:3]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)=[O:8]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 85301016Methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl)-3-pentenoate

Product 1

HCID 109262505-Isoxazoleacetic acid, 3,4-bis(4-methoxyphenyl)-, methyl esterYield 90%

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 176Acetic AcidSolvent

Procedure

A 3.7 g quantity of methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl)-3-pentenoate was heated at 60° C. with stirring for 24 hours in 40 ml of acetic acid in the presence of 0.4 g of cobalt acetate tetrahydrate while passing air through the mixture. After addition of 3N sulfuric acid, the reaction mixture was subjected to extraction with ethyl acetate, and the organic layer was washed with a saturated solution of potassium carbonate and then with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The organic layer was concentrated at a reduced pressure, and the residue was subjected to silica gel column chromatography (eluants: ethyl acetate-n-hexane) for separation and purification, giving 3.3 g (yield 90%) of the above-identified compound as a while solid product.

Workup

  1. extractionthe reaction mixture was subjected to extraction with ethyl acetate
  2. washthe organic layer was washed with a saturated solution of potassium carbonate
  3. dry with materialwith a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer was concentrated at a reduced pressure
  5. customthe residue was subjected to silica gel column chromatography (eluants: ethyl acetate-n-hexane) for separation and purification

Sources & evidence

ORD record
ord-5537fd3dbb9b4345810c43e41dfd389b
Source dataset
uspto-grants-1994_05
Patent number
US05310926

Reaction notes

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