1-[(Trimethylsilyl)ethynyl]-4-(trifluoromethyl)benzene → 1-Ethynyl-4-(trifluoromethyl)benzene

HRID 1460989Notes

Reaction equation

HRID 1460989 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][Si](C)(C)C)=[CH:5][CH:4]=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)C>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[CH:5][C:6]([C:9]#[CH:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 41788871-[(Trimethylsilyl)ethynyl]-4-(trifluoromethyl)benzeneHCID 11726816Tetrabutylammonium Fluoride Trihydrate

Product 1

HCID 43482951-Ethynyl-4-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

This compound was prepared in a manner analogous to that of Example 1, Step C, using 19.0 grams (0.0784 mole) of 1-(4-trifluoromethylphenyl)-2-trimethylsilylethyne and 24.7 grams (0.0784 mole) of tetrabutylammonium fluoride trihydrate in 200 ml of diethyl ether. The reaction mixture was filtered through silica gel, and the silica gel was washed with diethylether. The wash and filtrate were combined and concentrated under reduced pressure yielding, 22.9 grams of ether concentrate which was predominantly 4-trifluoromethylphenylethyne.

Workup

  1. customThis compound was prepared in a manner analogous to that of Example 1, Step C
  2. filtrationThe reaction mixture was filtered through silica gel
  3. washthe silica gel was washed with diethylether
  4. washThe wash
  5. concentrationconcentrated under reduced pressure
  6. customyielding
  7. concentration22.9 grams of ether concentrate which

Sources & evidence

ORD record
ord-5f4e144463db49f680c6d1837630187d
Source dataset
uspto-grants-1991_12
Patent number
US05073564

Reaction notes

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