Réaction #74501

Équation de réaction

(3-bromonaphthalen-1-yl)methanol

imidazole

TIPSCl

→

title compound

Rendement 96.0%

((3-Bromonaphthalen-1-yl)methoxy)triisopropylsilane

Rendement 96.0%

Solvants

ammonium chloride

DMF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with EtOAc
2. 2
   LavageThe organic layer was washed with water
3. 3
   Séchagebrine, dried over anhydrous MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe crude residue was purified by column chromatography (3-10% EtOAc/hexanes)

Mode opératoire

To a solution of (3-bromonaphthalen-1-yl)methanol in DMF (100 mL) was added imidazole (6.4 g, 93 mmol), DMAP (0.57 g, 4.7 mmol), and TIPSCl (15 mL, 70 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 (17.9 g, 96%) as a colorless oil.

Source