Triethylamine → HCID 14076002, Verbindung

HRID 1649625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1649625
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:2]#[CH:3].C(N(CC)CC)C.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>C1(C)C=CC=CC=1.[Cu]Br>[CH3:20][C:19]([CH3:22])([C:18](=[O:23])[C:3]#[C:2][CH2:1][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH3:21]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 83613(Prop-2-ynyloxy)benzene

Produkt 1

HCID 14076002HCID 14076002, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24593copper(I) bromideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

13.2 g (0.1 mol) of phenyl propargyl ether are added dropwise to a mixture of 10.1 g (0.1 mol) of triethylamine and 1.43 g of copper-(I) bromide in 60 ml of toluene at 20° C., under a nitrogen atmosphere and with stirring. The mixture is subsequently stirred at 20° C. for 30 minutes. Thereafter, 12 g (0.1 mol) of pivaloyl chloride are added dropwise in the course of 15 minutes. The reaction mixture is heated to 80° C. and is stirred at this temperature for 10 hours. After cooling to room temperature, the reaction mixture is washed first with dilute aqueous hydrochloric acid and then with water. The organic phase is concentrated by stripping off the solvent and the residue which remains is distilled under a high vacuum. 16 g (75% of theory) of 2,2-dimethyl-6-phenoxyhex-4-in-3-one are obtained in this manner in the form of a liquid.

Aufarbeitung

  1. stirringThe mixture is subsequently stirred at 20° C. for 30 minutes
  2. stirringis stirred at this temperature for 10 hours
  3. temperatureAfter cooling to room temperature
  4. washthe reaction mixture is washed first with dilute aqueous hydrochloric acid
  5. concentrationThe organic phase is concentrated
  6. distillationthe residue which remains is distilled under a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c1e76c84b03c475f9829981023074d3c
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04921529

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