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

HRID 2106963Notes

Reaction equation

HRID 2106963 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5a8fc49a27344bb2b9e97e10d8efe83e
Source dataset
uspto-grants-1990_06
Patent number
US04931591

Reaction notes

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