Reaktion #346972

Reaktionsgleichung

6-Bromo-2-naphthol

imidazole

t-butyldimethylsilyl chloride

imidazole

silyl chloride

→

solid

Ausbeute 74.1%

6-Bromo-2-(t-butyldimethylsilyloxy) naphthalene

Ausbeute 74.1%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigereaction
2. 2
   SonstigeAfter evaporation of DMF
3. 3
   Extraktionthe mixture was extracted with EtOAc and 5% aqueous KHSO4
4. 4
   Trocknendried (Na2SO4)
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe crude product was purified by silica gel chromatography
7. 7
   Wascheneluting with hexane

Vorschrift

6-Bromo-2-naphthol (10 g, 44 mmol), imidazole (7.4 g, 110 mmol), and t-butyldimethylsilyl chloride (10 g, 66 mmol) were stirred in DMF (50 mL) at room temperature overnight. TLC analysis indicated incomplete reaction, so additional imidazole (0.6 g) and silyl chloride (1.3 g) were added, and stirring continued 1 day. After evaporation of DMF, the mixture was extracted with EtOAc and 5% aqueous KHSO4, dried (Na2SO4), and evaporated. The crude product was purified by silica gel chromatography, eluting with hexane, to yield a colorless solid (11 g). mp 62°-63° C. 1H NMR (300 MHz, CDCl3): 7.90 (d, 1H, J=l Hz), 7.62 (d, 1H, J=9 Hz), 7.55 (d, 1H, J=9 Hz), 7.46 (dd, 1H, J=9, 2 Hz), 7.14 (d, 1H, J=2 Hz), 7.08 (dd, 1H, J=9,2 Hz), 1.00 (s, 9H), 0.23 (s, 6H). MS(CH4): 365 (20%, M+C2H5, 1 Br isotope pattern), 337 (base, M+H, 1 Br isotope pattern).

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