Hydrogen Peroxide → 5-Isoxazoleacetic acid, 3,4-bis(4-methoxyphenyl)-, methyl ester

HRID 1033533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1033533
[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].[Mn]([O-])(=O)(=O)=O.[K+].OO>ClCCl.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]

Komponenten

6

Edukt 3

HCID 784Hydrogen PeroxideHCID 516875Potassium PermanganateHCID 85301016Methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl)-3-pentenoate

Produkt 1

HCID 109262505-Isoxazoleacetic acid, 3,4-bis(4-methoxyphenyl)-, methyl esterAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A 1.75 g (5 mmols) quantity of methyl 5-hydroxyimino-4,5-bis(4-methoxyphenyl)-3-pentenoate was dissolved in 8.5 ml of dichloromethane and 4 ml of acetic acid, then 0.79 g of potassium permanganate was slowly added to the solution at room temperature, and the mixture was stirred for 4 hours. After the completion of reaction, a hydrogen peroxide solution was added to the reaction mixture until the mixture became transparent. The mixture was diluted with 10 ml of dichloromethane, subsequently washed with water, with sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride successively, and dried over anhydrous magnesium sulfate. The dried product was subjected to silica gel column chromatography (eluants: ethyl acetate-n-hexane) for separation and purification, affording 10.2 g (yield 60%) of the above-identified compound as a white solid product.

Aufarbeitung

  1. customAfter the completion of reaction
  2. washsubsequently washed with water, with sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe dried product was subjected to silica gel column chromatography (eluants: ethyl acetate-n-hexane) for separation and purification

Quellen und Nachweise

ORD-Eintrag
ord-4740e134e7034ee6a0703640086ca6ad
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05310926

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