Methyl iodide → trans-Glutaconic acid methyl ester

HRID 1057474Notes

Reaction equation

HRID 1057474 reaction equation
[C:1]([OH:9])(=[O:8])[CH:2]=[CH:3][CH2:4][C:5]([OH:7])=[O:6].[H-].[Na+].I[CH3:13]>CN(C=O)C>[CH3:13][O:6][C:5](=[O:7])/[CH:4]=[CH:3]/[CH2:2][C:1]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 74406Pentenedioic acid

Product 1

HCID 101278073trans-Glutaconic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of glutaconic acid in DMF (0.1 M) at 0° C. was added NaH (1 eq). After 15 min, iodomethane (1.2 eq) was added, and the mixture was allowed to warm to room temperature overnight. The reaction was quenched with saturated ammonium chloride, and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (silica; 10% MeOH/CHCl3) to afford a colorless viscous oil. EI-MS m/z 143 (M−H)−

Workup

  1. customThe reaction was quenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed (silica; 10% MeOH/CHCl3)
  8. customto afford a colorless viscous oil

Sources & evidence

ORD record
ord-3cd5b5b5e3d54a75bdcc47a84d5f5b82
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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