Reaktion #52317

Reaktionsgleichung

Water

Lithium hexamethyldisilazane

5-bromo-1H-indole

triisopropylsilyl chloride

→

title compound

Ausbeute 92.0%

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

Ausbeute 92.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 30 minutes
2. 2
   Sonstigeto quench
3. 3
   Sonstigethe reaction
4. 4
   Sonstigethe solvent was removed under reduced pressure
5. 5
   Sonstigeto give the crude mixture, which
6. 6
   Sonstigewas purified via column chromatography on silica gel (9:1 Hexane/ethyl acetate)

Vorschrift

Lithium hexamethyldisilazane [1.0 M] (44.7 mL, 44.4 mmol) was added to a solution of 5-bromo-1H-indole (7.30 g, 37.0 mmol) in tetrahydrofuran (50 mL) at room temperature. After stirring for 5 minutes, triisopropylsilyl chloride (8.62 g, 44.4 mmol) was added to reaction mixture and stirred for 30 minutes. Water was added to quench the reaction and the solvent was removed under reduced pressure to give the crude mixture, which was purified via column chromatography on silica gel (9:1 Hexane/ethyl acetate) to give the title compound in 92% yield. 1H NMR (CDCl3) δ 7.74 (d, J=1.8, 1H), 7.36 (d, J=8.8 Hz, 1H), 7.22 (m, 2H), 6.55 (d, J=3.1 Hz, 1H), 1.65 (m, 3H), 1.12 (d, J=7.5 Hz, 18H).

Quelle