Propargyl bromide → (2Z)-1,7,7-trimethyl-N-(prop-2-yn-1-yloxy)bicyclo[2.2.1]heptan-2-imine

HRID 1389408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1389408
[Na].[CH3:2][C:3]12[C:9]([CH3:11])([CH3:10])[CH:6]([CH2:7][CH2:8]1)[CH2:5][C:4]2=[N:12][OH:13].[CH2:14](Br)[C:15]#[CH:16]>CO>[CH2:16]([O:13][N:12]=[C:4]1[CH2:5][CH:6]2[C:9]([CH3:10])([CH3:11])[C:3]1([CH3:2])[CH2:8][CH2:7]2)[C:15]#[CH:14]

Komponenten

5

Edukt 3

HCID 7842Propargyl bromideHCID 26110Camphor, oximeHCID 5360545Sodium

Produkt 1

HCID 52692(2Z)-1,7,7-trimethyl-N-(prop-2-yn-1-yloxy)bicyclo[2.2.1]heptan-2-imineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

4.6 g (0.2 moles) of metallic sodium are dissolved in 200 ml of methanol, and 33.4 g (0.2 moles) of (±)-1,7,7-trimethyl-bicyclo[2,2,1]heptane-2-one-oxime are added to the solution. After one hour of boiling 23.8 g (0.2 moles) of propargyl bromide are introduced, and the reaction is continued for a further hour. The mixture is cooled, the separated sodium bromide is filtered off, the filtrate is concentrated, and the concentrate is subjected to fractional distillation in vacuo. 33.2 g (81%) of (±)-2-(propargyloxyimino)-1,7,7-trimethyl-bicyclo[2,2,1]heptane are obtained as a light yellow oil; b.p.: 94° C./1.5 mm Hg, nD20 =1.4955.

Aufarbeitung

  1. waitthe reaction is continued for a further hour
  2. temperatureThe mixture is cooled
  3. filtrationthe separated sodium bromide is filtered off
  4. concentrationthe filtrate is concentrated
  5. distillationthe concentrate is subjected to fractional distillation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b639f6dc1b3044a8833c16a1689a1b41
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04244888

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