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

HRID 466514Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 466514
[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]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 15021947HCID 15021947, Verbindung

Produkt 1

HCID 30656912,6,7-Trioxabicyclo(2.2.2)octane, 4-ethyl-1-(4-ethynylphenyl)-Ausbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0ba9c90cf93d4c4d9929597069f5025e
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157029

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