反応 #1447121

反応方程式

tert-butyl 5-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole-1-carboxylate

TBAF

→

title compound

tert-butyl 5-hydroxy-1H-indole-1-carboxylate

溶媒

THF

反応条件

後処理

1. 1
   その他to reach room temperature
2. 2
   その他The reaction was quenched by the addition of saturated aqueous NH4Cl solution
3. 3
   抽出extracted with ethyl acetate
4. 4
   洗浄The organic layer was washed with H2O, brine
5. 5
   乾燥dried over Na2SO4
6. 6
   その他The crude product was purified by column chromatography on silica gel (Petroleum ether:EtOAc 92/8)

実験手順

A solution (0.18 M) of tert-butyl 5-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole-1-carboxylate in THF was treated with TBAF (1.1 eq) at 0° C. The mixture was stirred at that temperature for 10 min and allowed to reach room temperature. The reaction was quenched by the addition of saturated aqueous NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with H2O, brine and dried over Na2SO4. The crude product was purified by column chromatography on silica gel (Petroleum ether:EtOAc 92/8) to afford the title compound as a colorless oil.

出典