Reaktion #59829

Reaktionsgleichung

ethyl acetate

ethyl 2-bromoisobutyrate

2-(4-bromophenyl)ethanol

sodium hydride

→

title compound

Ausbeute 15.2%

Ethyl 2-[2-(4-bromophenyl)ethoxy]-2-methylpropionate

Ausbeute 15.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 12 hours
2. 2
   Sonstigea saturated aqueous ammonium chloride solution, and the organic layer was separated
3. 3
   ExtraktionThe aqueous layer was extracted twice with ethyl acetate
4. 4
   SonstigeThe organic layer was collected
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvent was evaporated under reduced pressure
8. 8
   SonstigeThe resultant was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Vorschrift

To a solution of 2-(4-bromophenyl)ethanol (1 g, 5 mmol) in THF (15 ml) was added sodium hydride (60% in parafin liquid) (220 mg, 5.5 mmol) at 0° C., and the mixture was stirred at room temperature for 15 minutes. To the mixture was added ethyl 2-bromoisobutyrate (1.08 g, 5.5 mmol), and the mixture was stirred at room temperature for 12 hours. To this reaction solution were added ethyl acetate and a saturated aqueous ammonium chloride solution, and the organic layer was separated. The aqueous layer was extracted twice with ethyl acetate, and the extracts were combined with the organic layer. The organic layer was collected, dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The resultant was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give the title compound (240 mg, 15%).

Quelle