p-Toluenesulfonic acid → 3-[(5,6-Difluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

HRID 1669762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669762
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([CH:13]=O)=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([CH3:15])[O:7]2.[CH3:17][C:18](=[O:23])[CH2:19][C:20](=[O:22])[CH3:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([CH:13]=[C:19]([C:18](=[O:23])[CH3:17])[C:20](=[O:22])[CH3:21])=[C:8]2[C:3]=1[C:4](=[O:16])[CH:5]=[C:6]([CH3:15])[O:7]2

Komponenten

6

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 31261AcetylacetoneHCID 574388895,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde

Produkt 1

HCID 575033293-[(5,6-Difluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

250 mg (1.12 mmol) of 5,6-difluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde, 0.14 ml (1.34 mmol) of 2,4-pentanedione and 212.1 mg (1.12 mmol) of para-toluenesulfonic acid are heated in 100 ml of toluene under reflux with a water trap for 10 h. After cooling, 100 ml of ethyl acetate are added, and the reaction mixture is washed with water and with brine. Drying of the organic phase and concentration result in 269.7 mg (79% of theory) of the title compound as beige-coloured crystals.

Aufarbeitung

  1. temperatureunder reflux with a water trap for 10 h
  2. temperatureAfter cooling
  3. washthe reaction mixture is washed with water and with brine
  4. customDrying of the organic phase and concentration

Quellen und Nachweise

ORD-Eintrag
ord-bb471bf970f44329b7fbb06869ef416b
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989633B2

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