Tetrabutylammonium Fluoride → HCID 21468934, compound

HRID 976562Notes

Reaction equation

HRID 976562 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([Si](C(C)C)(C(C)C)C(C)C)[CH:31]=[CH:30]2)#[N:20]>C1COCC1.[Cl-].[Na+].O>[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH:31]=[CH:30]2)#[N:20]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21468966HCID 21468966, compound

Product 1

HCID 21468934HCID 21468934, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Tetra-n-butylammonium fluoride (8.0 mmoles, 8 ml of 1.0M solution in THF) was added to 5-(2-Cyanophenyl)-1-triisopropylsilylindole (4 mmole, 1.5 g) in 5 ml THF and stirred at room temperature for 5 minutes. The reaction was added to brine and extracted with ether. The ether solution was dried over sodium sulfate and concentrated. The residue was chromatographed over silica gel eluted with chloroform to yield 0.69 g of 5-(2-cyanophenyl)indole. (MS)

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether solution was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was chromatographed over silica gel
  5. washeluted with chloroform

Sources & evidence

ORD record
ord-bc4d45b6f4624315964c06e11a16af87
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

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