تفاعل #1239

معادلة التفاعل

tert-butyldimethylsilyl chloride

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

DMF

triethylamine

→

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

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with ethyl ether
2. 2
   أخرىthe organic phase decanted
3. 3
   تجفيفdried over magnesium sulfate
4. 4
   أخرىevaporated
5. 5
   أخرىThe residue obtained
6. 6
   أخرىwas purified by chromatography on a silica column
7. 7
   غسيلeluted with heptane
8. 8
   أخرى12 g (76%) of 7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene of melting point 120°-121° C. were recovered

الإجراء التجريبي

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.

المصدر