Reaktion #1447121

Reaktionsgleichung

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

TBAF

→

title compound

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto reach room temperature
2. 2
   SonstigeThe reaction was quenched by the addition of saturated aqueous NH4Cl solution
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with H2O, brine
5. 5
   Trocknendried over Na2SO4
6. 6
   SonstigeThe crude product was purified by column chromatography on silica gel (Petroleum ether:EtOAc 92/8)

Vorschrift

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.

Quelle