Ethyl Acetate → 5-Isoxazoleacetic acid, 3,4-bis(4-methoxyphenyl)-, methyl ester

HRID 847533Notes

Reaction equation

HRID 847533 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].BrN1C(=O)CCC1=O.C(OCC)(=O)C>C1C=CC=CC=1>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:3]2[C:4]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:5]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[O:1][N:2]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 85301016Methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl)-3-pentenoate

Product 1

HCID 109262505-Isoxazoleacetic acid, 3,4-bis(4-methoxyphenyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 50 g of benzene was dissolved 3.05 g of methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl-3-pentenoate obtained in Example 3. Thereto was added gradually 3.91 g of N-bromosuccinimide at room temperature and the mixture was stirred at the same temperature for 2 hours. After completion of the reaction, ethyl acetate was added to the reaction mixture for dilution, and the organic layer was washed with an aqueous 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) and crystallized from ether, giving the above-identified compound.

Workup

  1. additionwas added to the reaction mixture for dilution
  2. washthe organic layer was washed with an aqueous 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. customcrystallized from ether
  6. customgiving the above-identified compound

Sources & evidence

ORD record
ord-d6bd34ae8c6041b48afcb4da92393a04
Source dataset
uspto-grants-1992_08
Patent number
US05142091

Reaction notes

Loading…