Hydracrylonitrile → 1-[(2-Cyanoethoxycarbonyl)methyl]-1-Cyclohexane Acetic Acid

HRID 584539

Reaktionsgleichung

Reaktionsgleichung von HRID 584539
C([Li])CCC.[OH:6][CH2:7][CH2:8][C:9]#[N:10].[C:11]12([CH2:22][C:21](=[O:23])[O:20][C:18](=[O:19])[CH2:17]1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2>C1COCC1>[C:9]([CH2:8][CH2:7][O:6][C:21]([CH2:22][C:11]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:23])#[N:10]

Komponenten

5

Edukt 3

HCID 8011HydracrylonitrileHCID 27342891,1-Cyclohexanediacetic AnhydrideHCID 178418339Butyllithium

Produkt 1

HCID 223409601-[(2-Cyanoethoxycarbonyl)methyl]-1-Cyclohexane Acetic AcidAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

8.2 mL of 1.6M butyllithium was added to a −78° C. solution of 3-hydroxy-propionitrile (13.19 mmol) in 50 mL of THF. The reaction mixture was warmed to 30° C. and stirred for 30 minutes. Then, a solution of 1,1-cyclohexanediacetic anhydride (10.99 mmol) in 10 mL of THF was added dropwise. The reaction mixture was warmed to room temperature over a period of one hour and stirred at room temperature with monitoring by TLC. When the reaction was judged complete, the reaction mixture was quenched with saturated ammonium chloride solution and THF was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate, washed with brine and dried over Na2SO4. After concentration in vacuo the residue was purified on silica gel (5% methanol in dichloromethane) to afford 2.64 g (95%) of the title compound. 1H NMR (CDCl3): δ 4.28 (2H, t, J=6.4 Hz); 2.71 (2H, t, J=6.4 Hz); 2.61 (4H, m); 1.52-1.42 (10H, m).

Aufarbeitung

  1. temperatureThe reaction mixture was warmed to room temperature over a period of one hour
  2. stirringstirred at room temperature with monitoring by TLC
  3. customthe reaction mixture was quenched with saturated ammonium chloride solution and THF
  4. customwas removed under reduced pressure
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationAfter concentration in vacuo the residue
  9. customwas purified on silica gel (5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-30d173f59c574ee48960bf4063419415
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927036B2

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