Chloroacetonitrile → Cyanomethyl-(alpha-naphthylmethyl)-malonic acid diethyl ester

HRID 2106961

Reaktionsgleichung

Reaktionsgleichung von HRID 2106961
[C:1]([CH2:3]C(CC1C2C(=CC=CC=2)C=CC=1)C(O)=O)#[N:2].[CH2:19]([O:21][C:22](=[O:40])[CH:23]([CH2:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH3:20].ClCC#N.[H-].[Na+]>CN(C=O)C>[CH2:27]([O:26][C:24](=[O:25])[C:23]([CH2:3][C:1]#[N:2])([CH2:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1)[C:22]([O:21][CH2:19][CH3:20])=[O:40])[CH3:28]

Komponenten

6

Edukt 4

HCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 9972002Diethyl (1-naphthyl)methylmalonateHCID 230496412(R,S)-Cyanomethyl-3-alpha-naphthylpropionic acid

Produkt 1

HCID 54438257Cyanomethyl-(alpha-naphthylmethyl)-malonic acid diethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2(R,S)-Cyanomethyl-3-α-naphthylpropionic acid: 3.0 g of α-naphthylmethylmalonic acid diethyl ester and, after 30 minutes, 0.6 ml of chloroacetonitrile are added to a stirred suspension of 0.44 g of sodium hydride dispersion in 50 ml of DMF. The reaction mixture is stirred for 1 hour at 50° and then concentrated by evaporation in a high vacuum. The residue is dissolved in ethyl acetate, washed with 0.1N hydrochloric acid and water, dried over sodium sulphate, concentrated by evaporation and purified by chromatography on silica gel with toluene, yielding cyanomethyl-(α-naphthylmethyl)-malonic acid diethyl ester.

Aufarbeitung

  1. concentrationconcentrated by evaporation in a high vacuum
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed with 0.1N hydrochloric acid and water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. custompurified by chromatography on silica gel with toluene

Quellen und Nachweise

ORD-Eintrag
ord-649492dd713142d8b52fc300f269f0d0
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04931591

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