Tetrabutylammonium Fluoride → 2-Phenyl-1H-indol-4-ol

HRID 1107624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1107624
[Si]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:13]2)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH:13]2

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 211830744-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-phenyl-1H-indole

Produkt 1

HCID 167416562-Phenyl-1H-indol-4-olAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-t-Butyldimethylsilyoxy-2-phenylindole (55 mg, 0.17 mmol) was dissolved in THF (10 ml) at 0° C. and treated with tetrabutylammonium flouride (0.5 ml, 1.0 M in THF, excess). After stirring at this temperature for 10 minutes, the reaction was quenched by addition of saturated ammonium chloride. The mixture was extracted several time with ethyl acetate, dried over magnesium sulfate, and evaporated to give a crude oil. Flash chromatography (5% ethyl acetate/hexanes) provided the desired phenol (30 mg, 84.8%) as a white solid. NMR. MS.

Aufarbeitung

  1. customthe reaction was quenched by addition of saturated ammonium chloride
  2. extractionThe mixture was extracted several time with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto give a crude oil

Quellen und Nachweise

ORD-Eintrag
ord-b99f6392b69a4ccab2ad60d30b662271
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06060492

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