Реакция #346972

Уравнение реакции

6-Bromo-2-naphthol

imidazole

t-butyldimethylsilyl chloride

imidazole

silyl chloride

→

solid

Выход 74.1%

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

Выход 74.1%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеreaction
2. 2
   ДругоеAfter evaporation of DMF
3. 3
   Экстракцияthe mixture was extracted with EtOAc and 5% aqueous KHSO4
4. 4
   Сушкаdried (Na2SO4)
5. 5
   Другоеevaporated
6. 6
   ДругоеThe crude product was purified by silica gel chromatography
7. 7
   Промывкаeluting with hexane

Методика

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).

Источник