Reacción #59829

Ecuación de reacción

ethyl acetate

ethyl 2-bromoisobutyrate

2-(4-bromophenyl)ethanol

sodium hydride

→

title compound

Rendimiento 15.2%

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

Rendimiento 15.2%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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%).

Fuente