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

HRID 345364Notes

Reaction equation

HRID 345364 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 tetrahydroforan) 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-9699f4cef7984ea5ab061c8806358406
Source dataset
uspto-grants-1991_10
Patent number
US05057508

Reaction notes

Loading…