Reaktion #1447120

Reaktionsgleichung

tert-butyldimethylsilyl chloride

5-hydroxyindole

imidazole

→

title compound

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

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed sequentially with H2O, 1N HCl (aq) and finally with brine
2. 2
   TrocknenThe combined organic fractions were dried over Na2SO4
3. 3
   SonstigeThe crude was purified by column chromatography on silica gel (Petroleum ether:Diethyl ether 90/10)

Vorschrift

To a stirred solution of 5-hydroxyindole in DCM (0.3 M) was added imidazole (2.0 eq). The mixture was cooled to 0° C. and treated with tert-butyldimethylsilyl chloride (1.0 eq). The resulting mixture was stirred at room temperature for 12 h, diluted with DCM, washed sequentially with H2O, 1N HCl (aq) and finally with brine. The combined organic fractions were dried over Na2SO4. The crude was purified by column chromatography on silica gel (Petroleum ether:Diethyl ether 90/10) to afford the title compound as a white solid.

Quelle