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

HRID 2260746Notes

Reaction equation

HRID 2260746 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 of methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl)-3-pentenoate in 40 ml of acetic acid was stirred at 60° C. for 24 hours while blowing air into the mixture in the presence of 0.4 g of cobalt acetate tetrahydrate. After completion of the reaction, 3N sulfuric acid was added to the solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous potassium carbonate solution and saturated brine in that order, and dried over anhydrous magnesium sulfate. The organic layer was then concentrated under reduced pressure and the residue was separated and purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give 3.3 g (yield 90%) of 5-methoxycarbonylmethyl-3,4-bis(4-methoxyphenyl)isoxazole.

Workup

  1. additionwas added to the solution
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous potassium carbonate solution and saturated brine in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was then concentrated under reduced pressure
  6. customthe residue was separated
  7. custompurified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-11df6311b43a49c596a1eb3b13ff2873
Source dataset
uspto-grants-1995_12
Patent number
US05478856

Reaction notes

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