Reaktion #634313

Reaktionsgleichung

Imidazole

t-butyldimethylsilyl chloride

ethyl vanillate

→

title compound

Ausbeute 104.5%

4-(t-butyl-dimethyl-silanyloxy)-3-methoxy-benzoic Acid Methyl Ester

Ausbeute 104.5%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe reaction solution was extracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and water
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by silica gel chromatography (hexane only to hexane

Vorschrift

Imidazole (3.47 g, 51.0 mmol) and t-butyldimethylsilyl chloride (3.84 g, 25.5 mmol) were added to a solution of ethyl vanillate (5.0 g, 25.5 mmol) in N,N-dimethylformamide (50 mL) at room temperature, and the mixture was stirred at room temperature for three hours. The reaction solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane only to hexane:ethyl acetate=10:1) to give the title compound (7.90 g, 100%).

Quelle