反応 #52317

反応方程式

Water

Lithium hexamethyldisilazane

5-bromo-1H-indole

triisopropylsilyl chloride

→

title compound

収率 92.0%

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

収率 92.0%

溶媒

tetrahydrofuran

反応条件

後処理

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

実験手順

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).

出典