Reacción #1447121

Ecuación de reacción

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

TBAF

→

title compound

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

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente