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

HRID 4589

Reaction equation

HRID 4589 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e9adca82e09c421dacd1f2f89a865ee9
Source dataset
uspto-grants-1988_02
Patent number
US04727060

Linked notes

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