Acetonitrile → HCID 69027529, compound

HRID 1790875Notes

Reaction equation

HRID 1790875 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:9][CH2:8][CH:7](Br)[C:6]=1[C:11]([O:13][CH3:14])=[O:12])=[O:4].[C:15](#[N:17])C>[C-]#N.C([N+](CC)(CC)CC)C>[CH3:1][O:2][C:3]([C:5]1[CH2:9][CH2:8][CH:7]([C:15]#[N:17])[C:6]=1[C:11]([O:13][CH3:14])=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 14376549HCID 14376549, compound

Product 1

HCID 69027529HCID 69027529, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 3014735Tetraethylammonium cyanideCatalyst

Procedure

3-Bromo-cyclopent-1-ene-1,2-dicarboxylic acid dimethyl ester was dissolved in acetonitril under inert conditions. Tetraethylammoniumcyanide (1.1 eq) was added in one portion. The mixture was stirred under inert gas until the reaction was finished (2 h monitored by TLC). The solvent was removed in vacuum and the residue was purified by flash chromatographie using a hexane/ethylacetat gradient to give 3-Cyano-cyclopent-1-ene-1,2-dicarboxylic acid dimethyl ester in 25% yield.

Workup

  1. custom(2 h monitored by TLC)
  2. customThe solvent was removed in vacuum
  3. customthe residue was purified by flash chromatographie

Sources & evidence

ORD record
ord-f0be5e581c264314b717384afeda3cb5
Source dataset
uspto-grants-2006_07
Patent number
US07071355B2

Reaction notes

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