Reaktion #73422

Reaktionsgleichung

1-(tert-Butyl-dimethyl-silanyl)-4-chloro-1H-indol-5-ol

TBAF

→

title compound

4-Chloro-1H-indol-5-ol

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 1 hour the reaction is quenched with ammonium chloride
2. 2
   workup.ADDITIONThe reaction is diluted with ethyl acetate
3. 3
   Waschenwashed with water
4. 4
   SonstigeThe organic phase is removed
5. 5
   Trocknendried (sodium sulfate)
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe mixture is absorbed onto silica
8. 8
   Sonstigepurified via FCC (0-40% ethyl acetate:heptanes)

Vorschrift

1-(tert-Butyl-dimethyl-silanyl)-4-chloro-1H-indol-5-ol (5.35 g, 18.98 mmol) is dissolved in THF (90 mL) and cooled to 0° C. TBAF (4.96 g, 18.98 mmol) is added over 5 minutes to the brown solution. After 1 hour the reaction is quenched with ammonium chloride. The reaction is diluted with ethyl acetate and washed with water and then brine. The organic phase is removed, dried (sodium sulfate) and concentrated. The mixture is absorbed onto silica and purified via FCC (0-40% ethyl acetate:heptanes) to obtain the title compound as a solid. MS (ESI) m/z 168.15 (M+1).

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