1-(4-Methoxyphenyl)butane-1,3-dione → 4-(4-Methoxybenzoyl)-5-methylisoxazole-3-carboxylic acid ethyl ester

HRID 887048

Reaktionsgleichung

Reaktionsgleichung von HRID 887048
[O-]CC.[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:18])[CH2:14][C:15](=[O:17])[CH3:16])=[CH:9][CH:8]=1.Cl[C:20](=[N:26]O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[CH2:24]([O:23][C:21]([C:20]1[C:14]([C:13](=[O:18])[C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:12][CH:11]=2)=[C:15]([CH3:16])[O:17][N:26]=1)=[O:22])[CH3:25]

Komponenten

5

Edukt 3

HCID 776401-(4-Methoxyphenyl)butane-1,3-dioneHCID 2723922Sodium ethoxideHCID 6816376Ethyl chloro(hydroximino)acetate

Produkt 1

HCID 596520274-(4-Methoxybenzoyl)-5-methylisoxazole-3-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel4×

Versuchsvorschrift

To 7.04 mL of 21% sodium ethoxide in ethanol (18.8 mmol) in 60 mL ethanol at 0° C. was added 4.70 g of 1-(4-methoxyphenyl)butane-1,3-dione (17.1 mmol) in 60 mL ethanol dropwise over 24 minutes. After 30 min a solution of 2.59 g of ethyl chloro-(hydroximino)acetate (17.1 mmol) in 30 mL ethanol was added dropwise over 6 minutes. The reaction was warmed to room temperature slowly. When TLC indicated the reaction was complete, the reaction was concentrated in vacuo. Water and saturated NaHCO3 was added and the product extracted with ethyl acetate. The ethyl acetate extracts were dried with Na2SO4, filtered, and concentrated in vacuo. The crude material was purified via silica gel chromatography eluting with 8:1 hexane:ethyl acetate to give 4-(4-methoxybenzoyl)-5-methylisoxazole-3-carboxylic acid ethyl ester which was dried overnight under high vacuum to give 3.74 g (71.8%).

Aufarbeitung

  1. concentrationthe reaction was concentrated in vacuo
  2. additionWater and saturated NaHCO3 was added
  3. extractionthe product extracted with ethyl acetate
  4. dry with materialThe ethyl acetate extracts were dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified via silica gel chromatography
  8. washeluting with 8:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-8f43d294955747ae9d8d9980fb7b361b
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08247414B2

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