Tetrabutylammonium Fluoride → 1-(Hex-5-ynyl)-4-n-propyl-2,6-dioxabicyclo[2.2.2]octane

HRID 1197374Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197374
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C:22]12[CH2:29][CH2:28][C:25]([CH2:30][CH2:31][CH2:32][CH2:33][C:34]#[C:35][Si](C)(C)C)([O:26][CH2:27]1)[O:24][CH2:23]2)[CH2:20][CH3:21]>O1CCCC1>[CH2:30]([C:25]12[CH2:28][CH2:29][C:22]([CH2:19][CH2:20][CH3:21])([CH2:23][O:24]1)[CH2:27][O:26]2)[CH2:31][CH2:32][CH2:33][C:34]#[CH:35]

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 193733704-n-Propyl-1-(6-trimethylsilylhex-5-ynyl) 2,6-dioxabicyclo[2.2.2]octane

Produkt 1

HCID 193732891-(Hex-5-ynyl)-4-n-propyl-2,6-dioxabicyclo[2.2.2]octane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Tetrabutylammonium fluoride solution (1.0M., solution 4.0 ml.) was added to a stirred solution of 4-n-propyl-1-(6-trimethylsilylhex-5-ynyl)-2,6,-dioxabicyclo[2.2.2]octane in dry tetrahydrofuran (40 ml.) at 20° and the mixture was stirred for 1 hour. The solvent was removed in vacuo and the residue was extracted with diethyl ether and water. The ethereal extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was chromatographed on alumina eluting with dichloromethane:hexane 1:9, saturated with ammonia. 1-(Hex-5-ynyl)-4-n-propyl-2,6-dioxabicyclo[2.2.2]octane was obtained as a colourless oil (0.45 g.)

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. extractionthe residue was extracted with diethyl ether and water
  3. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on alumina eluting with dichloromethane:hexane 1:9, saturated with ammonia

Quellen und Nachweise

ORD-Eintrag
ord-85ee9095fa5e42559ffa6cb49e552239
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116862

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