Tetrabutylammonium Fluoride → HCID 23042569, compound

HRID 2165866Notes

Reaction equation

HRID 2165866 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C:22]12[CH2:29][O:28][C:25]([C:30]3[CH:35]=[CH:34][C:33]([C:36]#[C:37][Si](C)(C)C)=[CH:32][CH:31]=3)([O:26][CH2:27]1)[O:24][CH:23]2[C:42]([F:45])([F:44])[F:43])[CH2:20][CH3:21]>O1CCCC1>[C:36]([C:33]1[CH:32]=[CH:31][C:30]([C:25]23[O:28][CH2:29][C:22]([CH2:19][CH2:20][CH3:21])([CH2:27][O:26]2)[CH:23]([C:42]([F:44])([F:45])[F:43])[O:24]3)=[CH:35][CH:34]=1)#[CH:37]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23042570HCID 23042570, compound

Product 1

HCID 23042569HCID 23042569, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride solution (0.84 ml., 1M solution in tetrahydrofuran) was added to a stirred solution of 4-n-propyl-3-trifluoromethyl-1-[4-(2-trimethylsilylethynyl)phenyl]-2,6,7-trioxabicyclo[2,2,2]octane (0.28 g.) in dry tetrahydrofuran (5 mls). The mixture was stirred for 30 minutes at room temperature. The solvent was removed in vacuo and the residue was dissolved in dry diethyl ether. The ethereal solution was washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was recrystallised from hexane. 1-(4-Ethynylphenyl)-4-n-propyl-3-trifluoromethyl-2,6,7-trioxabicyclo[2,2,2]octane was obtained as a pale yellow solid (70 mg.).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dry diethyl ether
  3. washThe ethereal solution was washed with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated in vacuo
  6. customThe residue was recrystallised from hexane

Sources & evidence

ORD record
ord-e79281e0488147edbfbad91c0c5bd6eb
Source dataset
uspto-grants-1990_07
Patent number
US04942173

Reaction notes

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