Reaktion #74501

Reaktionsgleichung

(3-bromonaphthalen-1-yl)methanol

imidazole

TIPSCl

→

title compound

Ausbeute 96.0%

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

Ausbeute 96.0%

Lösungsmittel

ammonium chloride

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc
2. 2
   WaschenThe organic layer was washed with water
3. 3
   Trocknenbrine, dried over anhydrous MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude residue was purified by column chromatography (3-10% EtOAc/hexanes)

Vorschrift

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.

Quelle