1-Chloromethylnaphthalene → 2-Cyanoethyl-alpha-naphthylmethylmalonic acid diethyl ester

HRID 2106960Notes

Reaction equation

HRID 2106960 reaction equation
C(CCC([CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)C(O)=O)#N.[CH2:20]([O:22][C:23](=[O:34])[CH:24]([CH2:30][CH2:31][C:32]#[N:33])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH3:21].[H-].[Na+].ClCC1C2C(=CC=CC=2)C=CC=1>CN(C=O)C>[CH2:28]([O:27][C:25](=[O:26])[C:24]([CH2:30][CH2:31][C:32]#[N:33])([CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[C:23]([O:22][CH2:20][CH3:21])=[O:34])[CH3:29]

Participants

6

Reactant 4

HCID 68451-ChloromethylnaphthaleneHCID 24758Sodium hydrideHCID 87005Diethyl (2-cyanoethyl)malonateHCID 230496424-Cyano-2(R,S)-alpha-naphthylmethylbutyric acid

Product 1

HCID 543236892-Cyanoethyl-alpha-naphthylmethylmalonic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-Cyano-2(R,S)-α-naphthylmethylbutyric acid: 2.13 g of 2-cyanoethylmalonic acid diethyl ester are added to a suspension of 0.48 g of sodium hydride dispersion in 25 ml of DMF. The reaction mixture is stirred for 2 hours at 80° and then, at room temperature, 1.77 g of α-chloromethylnaphthalene in 5 ml of DMF are added. The mixture is further stirred for 16 hours at 50° and then concentrated by evaporation. The residue is dissolved in ethyl acetate, washed with 0.1N hydrochloric acid and water, dried over sodium sulphate and concentrated by evaporation, leaving 2-cyanoethyl-α-naphthylmethylmalonic acid diethyl ester.

Workup

  1. stirringThe mixture is further stirred for 16 hours at 50°
  2. concentrationconcentrated by evaporation
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with 0.1N hydrochloric acid and water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-334a1d14687d468caaf2b81128b86081
Source dataset
uspto-grants-1990_06
Patent number
US04931591

Reaction notes

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