Diethylamine → 1-(2,2-Diethoxyethyl)cyclohexane-1-carbonitrile

HRID 620922

Reaktionsgleichung

Reaktionsgleichung von HRID 620922
C(NCC)C.C([Li])CCC.[CH:11]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[CH2:23]Br)[CH3:20]>CCCCCC>[CH2:19]([O:21][CH:22]([O:25][CH2:26][CH3:27])[CH2:23][C:11]1([C:17]#[N:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH3:20]

Komponenten

6

Edukt 4

HCID 8021DiethylamineHCID 69834CyanocyclohexaneHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 178418339Butyllithium

Produkt 1

HCID 132173501-(2,2-Diethoxyethyl)cyclohexane-1-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

51.7 ml (0.5 mol) of anhydrous diethylamine are added dropwise, under protective gas at -10° C., to 312.5 ml (0.5 mol) of a 15% strength solution of n-butyllithium in hexane. The mixture is stirred for 20 minutes and then cooled to -70° C. 54.6 g of cyclohexanecarbonitrile are added dropwise over the course of 30 minutes and, after a further 30 minutes, 98.5 g of bromoacetaldehyde diethyl acetal are added within 1 hour and the mixture is left at low temperature for 24 hours. It is then warmed to room temperature, 100 g of ice are added, and the mixture is extracted twice with 500 ml of ethyl acetate, and the organic phase is dried over sodium sulfate, evaporated in vacuo and the residue is subjected to vacuum distillation.

Aufarbeitung

  1. waitthe mixture is left at low temperature for 24 hours
  2. temperatureIt is then warmed to room temperature
  3. extractionthe mixture is extracted twice with 500 ml of ethyl acetate
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. customevaporated in vacuo
  6. distillationthe residue is subjected to vacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-c95d3c5d99e543bf941100058e7e16a4
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04822894

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