Acrylonitrile → (2-Cyanoethyl)-alpha-naphthoxymalonic acid diethyl ester

HRID 4591

Reaktionsgleichung

Reaktionsgleichung von HRID 4591
[C:1]([CH2:3][CH2:4]C(OC1C2C(=CC=CC=2)C=CC=1)C(O)=O)#[N:2].[OH-].[K+].[CH2:22]([O:24][C:25](=[O:43])[CH:26]([O:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1)[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:23].C(#N)C=C>C(OCC)(=O)C>[CH2:30]([O:29][C:27](=[O:28])[C:26]([CH2:4][CH2:3][C:1]#[N:2])([O:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1)[C:25]([O:24][CH2:22][CH3:23])=[O:43])[CH3:31]

Komponenten

6

Edukt 4

HCID 7855AcrylonitrileHCID 14797Potassium HydroxideHCID 230496484-Cyano-2(R,S)-alpha-naphthoxybutyric acidHCID 54105534alpha-Naphthoxymalonic acid diethyl ester

Produkt 1

HCID 54279623(2-Cyanoethyl)-alpha-naphthoxymalonic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Cyano-2(R,S)-α-naphthoxybutyric acid: 0.11 ml of a 50% aqueous KOH solution is added at 0°, while stirring, to a mixture of 5.0 g of α-naphthoxymalonic acid diethyl ester and 1.09 ml of acrylonitrile. The reaction mixture is stirred for 5 days at room temperature and then dissolved in ethyl acetate. The ethyl acetate solution is washed with 2N sodium bicarbonate solution, 2N hydrochloric acid and brine, dried over sodium sulphate and concentrated by evaporation, leaving (2-cyanoethyl)-α-naphthoxymalonic acid diethyl ester.

Aufarbeitung

  1. washThe ethyl acetate solution is washed with 2N sodium bicarbonate solution, 2N hydrochloric acid and brine
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-0c2d879632c7416297f9a04382172ffc
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727060

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