Tetrabutylammonium Fluoride → 2,6,7-Trioxabicyclo(2.2.2)octane, 4-ethyl-1-(4-ethynylphenyl)-

HRID 466514Notes

Reaction equation

HRID 466514 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C:21]12[CH2:28][O:27][C:24]([C:29]3[CH:34]=[CH:33][C:32]([C:35]#[C:36][Si](C)(C)C)=[CH:31][CH:30]=3)([O:25][CH2:26]1)[O:23][CH2:22]2)[CH3:20]>O1CCCC1>[CH2:19]([C:21]12[CH2:26][O:25][C:24]([C:29]3[CH:30]=[CH:31][C:32]([C:35]#[CH:36])=[CH:33][CH:34]=3)([O:23][CH2:22]1)[O:27][CH2:28]2)[CH3:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15021947HCID 15021947, compound

Product 1

HCID 30656912,6,7-Trioxabicyclo(2.2.2)octane, 4-ethyl-1-(4-ethynylphenyl)-Yield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutyl ammonium fluoride solution (3.3 ml, 1M in tetrahydrofaran) was added to a stirred solution of 4-ethyl-1-[4-(2-trimethylsilylethynyl)-phenyl]2,6,7-trioxabicyclo[2,2,2]octane (0.87 gms) in tetrahydrofuran (15 ml). The mixture was stirred for 30 minutes at room temperature when the solvent was removed under vacuum. The residue was taken up in ether and washed with water and brine. The ethereal solution was dried over anhydrous magnesium sulphate and evaporated in vacuo. Recrystallisation from hexane gave 4-ethyl-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo[2,2,2]octane as an off-white solid (0.66 gms).

Workup

  1. customwas removed under vacuum
  2. washwashed with water and brine
  3. dry with materialThe ethereal solution was dried over anhydrous magnesium sulphate
  4. customevaporated in vacuo
  5. customRecrystallisation from hexane

Sources & evidence

ORD record
ord-0ba9c90cf93d4c4d9929597069f5025e
Source dataset
uspto-grants-1992_10
Patent number
US05157029

Reaction notes

Loading…