Acetonitrile → 2,2-Dimethyl-3-oxopentanedinitrile

HRID 1930364Notes

Reaction equation

HRID 1930364 reaction equation
[C:1](#[N:3])[CH3:2].[H-].[Na+].[C:6]([C:8]([CH3:14])([CH3:13])[C:9](OC)=[O:10])#[N:7]>C1COCC1>[CH3:13][C:8]([CH3:14])([C:9](=[O:10])[CH2:2][C:1]#[N:3])[C:6]#[N:7]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 109645102-Cyano-2-methyl-propanoic acid methyl ester

Product 1

HCID 866201652,2-Dimethyl-3-oxopentanedinitrileYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of anhydrous acetonitrile (2.3 g, 56 mmol) in THF (100 mL) was added dropwise at 80° C. to a mixture of NaH (60%, 2.8 g, 70 mmol) and methyl 2-cyano-2-methylpropanoate (6 g, 47 mmol) in THF (100 mL). The resultant reaction mixture was heated at reflux for 8 hours. The solvent was removed in vacuo and the residue was diluted with EtOAc and washed with 10% HCl, water and brine. The organics were dried (MgSO4) and concentrated in vacuo to obtain crude 2,2-dimethyl-3-oxopentanedinitrile (4 g), which was used for the next step reaction without further purification.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 8 hours
  4. customThe solvent was removed in vacuo
  5. additionthe residue was diluted with EtOAc
  6. washwashed with 10% HCl, water and brine
  7. dry with materialThe organics were dried (MgSO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2620d43eca804230a17540b8355a09b9
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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