반응 #52317

반응 방정식

Water

Lithium hexamethyldisilazane

5-bromo-1H-indole

triisopropylsilyl chloride

→

title compound

수율 92.0%

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

수율 92.0%

용매

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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).

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