Реакция #1239

Уравнение реакции

tert-butyldimethylsilyl chloride

7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene

DMF

triethylamine

→

7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene

Растворители

water

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl ether
2. 2
   Другоеthe organic phase decanted
3. 3
   Сушкаdried over magnesium sulfate
4. 4
   Другоеevaporated
5. 5
   ДругоеThe residue obtained
6. 6
   Другоеwas purified by chromatography on a silica column
7. 7
   Промывкаeluted with heptane
8. 8
   Другое12 g (76%) of 7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene of melting point 120°-121° C. were recovered

Методика

11.9 g (33.3 mmol) of 7-(1-adamantyl)-6-hydroxy-2-bromonaphthalene, 120 ml of DMF, 5.1 ml (36.6 mmol) of triethylamine and 203 mg of 4-dimethylaminopyridine were introduced successively into a three-necked flask. A solution of 5.52 g (36.6 mmol) of tert-butyldimethylsilyl chloride was added dropwise and the mixture was stirred at room temperature for 12 hours. The reaction medium was poured into water, extracted with ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with heptane; 12 g (76%) of 7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene of melting point 120°-121° C. were recovered.

Источник