Malononitrile → 2-((3-Ethoxy-4-methoxyphenyl)(hydroxy)methylene)malononitrile

HRID 238061Notes

Reaction equation

HRID 238061 reaction equation
[H-].[Na+].[C:3](#[N:7])[CH2:4][C:5]#[N:6].[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:14](Cl)=[O:15])[CH3:9]>C1COCC1>[CH2:8]([O:10][C:11]1[CH:12]=[C:13]([C:14]([OH:15])=[C:4]([C:3]#[N:7])[C:5]#[N:6])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH3:9]

Participants

5

Reactant 3

HCID 8010MalononitrileHCID 24758Sodium hydrideHCID 450812503-Ethoxy-4-methoxybenzoyl chloride

Product 1

HCID 866170182-((3-Ethoxy-4-methoxyphenyl)(hydroxy)methylene)malononitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

NaH (2.2 g, 56 mmol, 60% dispersion in paraffin oil) was added to a solution of malononitrile (1.85 g, 28 mmol) in THF (30 mL) on ice. 3-ethoxy-4-methoxybenzoyl chloride (25.5 mmol) was dissolved in THF (50 mL) and added the first solution dropwise by syringe at 0° C. The ice was then removed and the reaction was allowed to proceed at RT for 60 min. 1N HCl (100 mL) was added and the solution was extracted three times with EtOAc. The organic phase was dried with MgSO4, filtered, and concentrated in vacuo to give an orange solid that was taken onto the next step without further characterization.

Workup

  1. additionadded the first solution dropwise by syringe at 0° C
  2. customThe ice was then removed
  3. addition1N HCl (100 mL) was added
  4. extractionthe solution was extracted three times with EtOAc
  5. dry with materialThe organic phase was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give an orange solid

Sources & evidence

ORD record
ord-5b21a4eb5bfa4d2bb1345ebcc563b57e
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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