Tetrabutylammonium Fluoride → 2-Ethynyl-1,3-dimethylbenzene

HRID 1514928Notes

Reaction equation

HRID 1514928 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]#[C:10][Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCCCCC>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]#[CH:10]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 13007668(2,6-Dimethylphenylethynyl)-trimethylsilane

Product 1

HCID 130076692-Ethynyl-1,3-dimethylbenzene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To an ice cold solution of (2,6-dimethylphenylethynyl)-trimethylsilane from the previous step in THF (20 mL) was added tetrabutylammonium fluoride in THF (17 mL of 1 M solution) dropwise. After stirring 18 h, the solution was diluted with hexane and extracted with water and brine. The organic layer was dried, filtered, and solvent removed under reduced pressure. The residual oil was redissolved in hexane and filtered through a silica gel plug, then chromatographed using hexane as eluent to give 2,6-dimethylphenylacetylene.

Workup

  1. extractionextracted with water and brine
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customsolvent removed under reduced pressure
  5. dissolutionThe residual oil was redissolved in hexane
  6. filtrationfiltered through a silica gel plug
  7. customchromatographed

Sources & evidence

ORD record
ord-fd1b591e1cf845e7a9c82ec7b8025587
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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