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

HRID 1421437Notes

Reaction equation

HRID 1421437 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 167416562-Phenyl-1H-indol-4-olYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d27b720e32fa42938f40fcd3529cf8c8
Source dataset
uspto-grants-2000_06
Patent number
US06075040

Reaction notes

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