Reaktion #472036

Reaktionsgleichung

5-Bromoindole

triisopropylsilyl chloride

→

compound 8

Ausbeute 96.0%

5-Bromo-1-triisopropylsilanyl-1H-indole

Ausbeute 96.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to RT
2. 2
   TemperaturThe reaction mixture was again cooled to 0° C.
3. 3
   Temperaturto warm to room temperature
4. 4
   workup.STIRRINGwas stirred overnight
5. 5
   WaschenThe mixture was washed with 2.0 N H3PO4
6. 6
   Trocknenthe organic layer was dried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe residue was purified by flash silica chromatography (100% Hexanes)

Vorschrift

5-Bromoindole (2.5 g, 12.75 mmol) was dissolved in tetrahydrofuran (THF; 50 mL) and cooled to 0° C. and Sodium Hydride NaH (920 mg, 23 mmol, 60%) was added in portions. The mixture was allowed to warm to RT with stirring for 1 hour. The reaction mixture was again cooled to 0° C. and triisopropylsilyl chloride (TIPSCl; 2.78 mL, 13.1 mmol) was added dropwise. The mixture was allowed to warm to room temperature and was stirred overnight. The mixture was washed with 2.0 N H3PO4, and the organic layer was dried over MgSO4, filtered and evaporated. The residue was purified by flash silica chromatography (100% Hexanes) to give compound 8 as an oil (4.3 g; 96% yield; M+1=353.4)

Quelle