Tetrabutylammonium Fluoride → 5-Ethynyl-1H-indole

HRID 340253Notes

Reaction equation

HRID 340253 reaction equation
C([Si]([C:8]#[C:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:9]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)#[CH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 668932335-[(Triethylsilyl)ethynyl]-1H-indole

Product 1

HCID 178425855-Ethynyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-((triethylsilyl)ethynyl)-1H-indole (from the previous step) in THF (0.2 M) cooled at 0° C. was treated with a solution (0.5 eq.) of tetrabutylammonium fluoride in a dropwise fashion. The reaction mixture turned black and was continued to stir for 30 minutes before warming up to rt. TLC showed full conversion. The reaction was quenched with water and was extracted with diethylether. Combined organic layers were dried over anhydrous Na2SO4 and concentrated using rotary evaporator with minim heating. Chromatography (silica gel, diethylether) afforded the product 5-ethynyl-1H-indole as colorless oil.

Workup

  1. customThe reaction was quenched with water
  2. extractionwas extracted with diethylether
  3. dry with materialCombined organic layers were dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customevaporator with minim
  6. temperatureheating

Sources & evidence

ORD record
ord-9e541765ed964fadaf928b3a44be6293
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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