Reacción #74493

Ecuación de reacción

(4-bromonaphthalen-2-yl)methanol

imidazole

TIPSCl

→

title compound

Rendimiento 82.0%

((4-Bromonaphthalen-2-yl)methoxy)triisopropylsilane

Rendimiento 82.0%

Disolventes

ammonium chloride

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with EtOAc
2. 2
   LavadoThe organic layer was washed with water
3. 3
   Secadobrine, dried over anhydrous MgSO4
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe crude residue was purified by column chromatography (3-10% EtOAc/hexanes)

Procedimiento

To a solution of the (4-bromonaphthalen-2-yl)methanol in DMF (100 mL) was added imidazole (7.6 g, 112 mmol), DMAP (0.68 g, 5.6 mmol), and TIPSCl (18 mL, 84 mmol). The resulting solution was stirred at room temperature for 12 h, diluted with a saturated ammonium chloride and extracted with EtOAc. The organic layer was washed with water then brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (3-10% EtOAc/hexanes) to yield the title compound (19.6 g, 82%) as colorless oil.

Fuente