Reaktion #1148730

Reaktionsgleichung

acetic acid

acetophenone

ethyl 2-methylthiazol-4-carboxylate

sodium hydride

→

1-(2-methylthiazol-4-yl)-3-phenylpropan-1,3-dione

Ausbeute 88.4%

Lösungsmittel

water

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturof heating
2. 2
   Temperaturunder refluxing
3. 3
   TemperaturAfter the reaction solution was cooled
4. 4
   Extraktionthe resulting mixture was extracted with ethyl acetate
5. 5
   WaschenThe extracted solution was washed with water
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   SonstigeThe solvent was evaporated under reduced pressure
8. 8
   Sonstigethe residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1 (v/v))

Vorschrift

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.

Quelle