Tetrabutylammonium Fluoride → 4-Chloro-1H-indol-5-ol

HRID 450294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450294
C([Si](C)(C)[N:6]1[C:14]2[C:9](=[C:10]([Cl:16])[C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:16][C:10]1[C:11]([OH:15])=[CH:12][CH:13]=[C:14]2[C:9]=1[CH:8]=[CH:7][NH:6]2

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 674317611-(tert-Butyl-dimethyl-silanyl)-4-chloro-1H-indol-5-ol

Produkt 1

HCID 445500814-Chloro-1H-indol-5-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. customAfter 1 hour the reaction is quenched with ammonium chloride
  2. additionThe reaction is diluted with ethyl acetate
  3. washwashed with water
  4. customThe organic phase is removed
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe mixture is absorbed onto silica
  8. custompurified via FCC (0-40% ethyl acetate:heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-8159a39ff0f24191a21a1a8d63d23ac5
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486954B2

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