Reaktion #1239

Reaktionsgleichung

tert-butyldimethylsilyl chloride

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

DMF

triethylamine

→

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

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl ether
2. 2
   Sonstigethe organic phase decanted
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residue obtained
6. 6
   Sonstigewas purified by chromatography on a silica column
7. 7
   Wascheneluted with heptane
8. 8
   Sonstige12 g (76%) of 7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-bromonaphthalene of melting point 120°-121° C. were recovered

Vorschrift

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.

Quelle