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

HRID 1389410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1389410
Cl.[CH2:2]([CH:5]1C=CC=C[O:6]1)[C:3]#C.[CH3:11][C:12]12[C:18]([CH3:20])([CH3:19])[CH:15]([CH2:16][CH2:17]1)[CH2:14][C:13]2=O.[N:22]1C=CC=CC=1>C(O)C>[CH2:5]([O:6][N:22]=[C:13]1[CH2:14][CH:15]2[C:18]([CH3:20])([CH3:19])[C:12]1([CH3:11])[CH2:17][CH2:16]2)[C:2]#[CH:3]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 2537CamphorHCID 86737430HCID 86737430, Verbindung

Produkt 1

HCID 52692(2Z)-1,7,7-trimethyl-N-(prop-2-yn-1-yloxy)bicyclo[2.2.1]heptan-2-imineAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

59.0 g (0.55 moles) of propargyloxamine hydrochloride are added to a solution of 76 g (0.5 moles) of (±)-1,7,7-trimethyl-bicyclo[2,2,1]heptane-2-one in 225 ml of pyridine and 450 ml of dry ethanol. The reaction mixture is boiled for 3 hours and then it is evaporated in vacuo. The residue is diluted with water, and the aqueous mixture is extracted with dichloroethane. The dichloroethane solution is evaporated, and the residue is subjected to fractional distillation in vacuo. 76.0 g (74.0%) of (±)-2-(propargyloxyimino)-1,7,7-trimethyl-bicyclo[2,2,1]heptane are obtained as a light yellow oil; b.p.: 92° C./1.0 mm Hg, nD20 =1.4956.

Aufarbeitung

  1. customit is evaporated in vacuo
  2. additionThe residue is diluted with water
  3. extractionthe aqueous mixture is extracted with dichloroethane
  4. customThe dichloroethane solution is evaporated
  5. distillationthe residue is subjected to fractional distillation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a8411769db6245c2a62aead80e5cc045
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04244888

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