Dimethylformamide → 5-Hydroxy-7-isopropoxy-2-methylthiochromone

HRID 441057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 441057
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[S:14])[CH:5]=[C:6]([CH3:13])[O:7]2.C(=O)([O-])[O-].[K+].[K+].[CH:21](I)([CH3:23])[CH3:22].CN(C=O)C>O>[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:21]([CH3:23])[CH3:22])[CH:9]=[C:8]2[C:3]=1[C:4](=[S:14])[CH:5]=[C:6]([CH3:13])[O:7]2

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 1361024115,7-Dihydroxy-2-methylthiochromone

Produkt 1

HCID 1361364155-Hydroxy-7-isopropoxy-2-methylthiochromoneAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

6.88 g of 5,7-dihydroxy-2-methylthiochromone (30.35 mmol), 12.56 g of potassium carbonate (91.05 mmol), 6.07 ml of isopropyl iodide (60.70 mmol) and 150 ml DMF were stirred at 60° C. for 30 minutes. After addition of water, the reaction solution was extracted twice with ethyl acetate, and the organic layer was washed with saturated NaCl water and was then dried over sodium sulfate anhydride. The solvent was distilled off under reduced pressure, and the crude product was purified by flash column chromatography (hexane : ethyl acetate=4 : 1), to give 6.71 g of 5-hydroxy-7-isopropoxy-2-methylthiochromone (83% yield).

Aufarbeitung

  1. extractionthe reaction solution was extracted twice with ethyl acetate
  2. washthe organic layer was washed with saturated NaCl water
  3. dry with materialwas then dried over sodium sulfate anhydride
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe crude product was purified by flash column chromatography (hexane : ethyl acetate=4 : 1)

Quellen und Nachweise

ORD-Eintrag
ord-26b2e6f57c504c8581ab9d07c94e286f
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521216

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