Acetic Acid → 1-(2-Methylthiazol-4-yl)-3-phenylpropan-1,3-dione

HRID 2099846

Reaktionsgleichung

Reaktionsgleichung von HRID 2099846
[H-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[CH3:12][C:13]1[S:14][CH:15]=[C:16]([C:18](OCC)=[O:19])[N:17]=1.C(O)(=O)C>C1COCC1.O>[CH3:12][C:13]1[S:14][CH:15]=[C:16]([C:18](=[O:19])[CH2:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])[N:17]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 7410AcetophenoneHCID 24758Sodium hydrideHCID 293353Ethyl 2-methyl-1,3-thiazole-4-carboxylate

Produkt 1

HCID 222852021-(2-Methylthiazol-4-yl)-3-phenylpropan-1,3-dioneAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a boiling suspension of sodium hydride (60% in oil) (360 mg) in anhydrous THF (10 ml) was added dropwise a solution of acetophenone (720 mg) and ethyl 2-methylthiazol-4-carboxylate (1.20 g) in anhydrous THF (10 ml), followed by 10 minutes of heating under refluxing. After the reaction solution was cooled, a mixed solution of acetic acid (1 ml) and water (30 ml) was added thereto, and the resulting mixture was extracted with ethyl acetate. The extracted solution was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1 (v/v)) to obtain 1-(2-methylthiazol-4-yl)-3-phenylpropan-1,3-dione (1.3 g, 88%) as yellow crystals. Hereinafter, the compounds of Reference Examples 2 to 10 were obtained similarly.

Aufarbeitung

  1. temperatureof heating
  2. temperatureunder refluxing
  3. temperatureAfter the reaction solution was cooled
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extracted solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-c203852ddbd149b285cb60be463c060b
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569688B2

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