Tetrabutylammonium Fluoride → 5-Ethynyl-1H-indole

HRID 1479539Notes

Reaction equation

HRID 1479539 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-93d6a7be45534d8cb1af09e3e853755e
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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