Hydrochloric Acid → 1-[[4-(2-Hydroxyethyl)phenyl]methyl]cyclohexanecarbonitrile

HRID 274123

Reaktionsgleichung

Reaktionsgleichung von HRID 274123
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].CN1CCN(C)[C:15]1=[O:20].[CH:21]1([C:27]#[N:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.Cl.[CH3:30][CH2:31][CH2:32][CH2:33]CC>O1CCCC1.O>[OH:20][CH2:15][CH2:11][C:10]1[CH:30]=[CH:31][C:32]([CH2:33][C:21]2([C:27]#[N:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:8][CH:9]=1

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 7912DiisopropylamineHCID 8058HexaneHCID 69834CyanocyclohexaneHCID 178418339Butyllithium

Produkt 1

HCID 189996321-[[4-(2-Hydroxyethyl)phenyl]methyl]cyclohexanecarbonitrileAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

To a mixture maintained under nitrogen, of 5.6 g (54.9 mmoles) of diisopropylamine and 92 ml of dry tetrahydrofuran, cooled to -40° C., there is added dropwise 34.2 ml (54.7 mmoles) of a 1.6M solution of n-butyllithium in hexane, then 8.2 g of 1,3-dimethylimidazolidin-2-one. The mixture is thereafter cooled to -78° C. and is stirred 1/4 hour before adding 5.45 g (50 mmoles) of commercial cyclohexanecarbonitrile in solution in 82 ml of dry tetrahydrofuran. After having stirred 1 hour, at -78° C., 14.3 g (50 mmoles) of the compound prepared in example 26a is added. The temperature is kept for an additional 3 hours at -78° C., before being allowed to rise and the mixture is stirred 19 hours at room temperature. Waster is then added, the mixture is acidified with HCl and is stirred again for 1 hour, before diluting it with water and extracting the reaction mixture with ether. The organic phase, washed with water, dried over Na2SO4 is concentrated. The liquid obtained is purified by distillation to give 7.5 g (yield= 61.6%) of a yellow liquid. b.p.0.5 =130°-80° C.

Aufarbeitung

  1. temperatureThe mixture is thereafter cooled to -78° C.
  2. stirringAfter having stirred 1 hour, at -78° C.
  3. stirringthe mixture is stirred 19 hours at room temperature
  4. additionWaster is then added
  5. stirringis stirred again for 1 hour
  6. extractionextracting the reaction mixture with ether
  7. washThe organic phase, washed with water
  8. dry with materialdried over Na2SO4
  9. concentrationis concentrated
  10. customThe liquid obtained
  11. distillationis purified by distillation

Quellen und Nachweise

ORD-Eintrag
ord-e79af58b3a7a4b2a9d3bbdca7fcce1a1
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387709

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