Methyl Crotonate → Methyl 3-methyl-4-cyano-4-(2-cyano-3-pyridyl)butyrate

HRID 2292089Notes

Reaction equation

HRID 2292089 reaction equation
C[O-].[Na+].[C:4]([C:6]1[C:11]([CH2:12][C:13]#[N:14])=[CH:10][CH:9]=[CH:8][N:7]=1)#[N:5].[C:15]([O:20][CH3:21])(=[O:19])/[CH:16]=[CH:17]/[CH3:18]>C(O)(=O)C>[CH3:18][CH:17]([CH:12]([C:13]#[N:14])[C:11]1[C:6]([C:4]#[N:5])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH2:16][C:15]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 638132Methyl CrotonateHCID 46725983-(Cyanomethyl)pyridine-2-carbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 15598816Methyl 3-methyl-4-cyano-4-(2-cyano-3-pyridyl)butyrate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A catalytic amount of a 5% strength methanolic sodium methylate solution is added to a mixture of 4.9 g (0.03 mol) of 2-cyano-3-pyridylacetonitrile and 3.4 g (0.03 mol) of methyl crotonate with stirring at a rate such that the reaction temperature remains below 40° C. When the evolution of heat has subsided, the mixture is neutralized using dilute acetic acid. The mixture is extracted with chloroform and the organic phase is dried over MgSO4, filtered and concentrated in vacuo. The residue is purified over a silica gel column using chloroform as eluent.

Workup

  1. customremains below 40° C
  2. temperatureWhen the evolution of heat
  3. extractionThe mixture is extracted with chloroform
  4. dry with materialthe organic phase is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified over a silica gel column

Sources & evidence

ORD record
ord-81f6d1dc7a84482bb222f75290f1ff7e
Source dataset
uspto-grants-1989_01
Patent number
US04801590

Reaction notes

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