반응 #1239

반응 방정식

tert-butyldimethylsilyl chloride

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

DMF

triethylamine

→

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

용매

water

반응 조건

후처리

1. 1
   추출extracted with ethyl ether
2. 2
   기타the organic phase decanted
3. 3
   건조dried over magnesium sulfate
4. 4
   기타evaporated
5. 5
   기타The residue obtained
6. 6
   기타was purified by chromatography on a silica column
7. 7
   세척eluted with heptane
8. 8
   기타12 g (76%) of 7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene of melting point 120°-121° C. were recovered

실험 절차

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.

출처