Pyrrolidine → 3-Fluoro-5-iodocinnamic Acid Methyl Ester

HRID 2095316Notes

Reaction equation

HRID 2095316 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([I:10])[CH:9]=1)[CH:5]=O.[C:11]([O:17][CH3:18])(=[O:16])[CH2:12]C([O-])=O.N1CCCC1>N1C=CC=CC=1>[CH3:18][O:17][C:11](=[O:16])[CH:12]=[CH:5][C:4]1[CH:7]=[C:8]([I:10])[CH:9]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 3801157Monomethyl malonateHCID 269863443-Fluoro-5-iodobenzaldehyde

Product 1

HCID 673095463-Fluoro-5-iodocinnamic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Fluoro-5-iodobenzaldehyde, monomethyl malonate, and a catalytic amount of pyrrolidine are heated in pyridine. After cooling, the solvent is distilled off in vacuo. 2N HCl and ethyl acetate are added to the residue, and the phases are separated. The organic layer is washed with brine and dried over Na2SO4. After evaporation, the residue is purified by CC on silica gel with EtOAc/hexane. Evaporation of appropriate fractions yields the title compound.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent is distilled off in vacuo
  3. addition2N HCl and ethyl acetate are added to the residue
  4. customthe phases are separated
  5. washThe organic layer is washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter evaporation
  8. customthe residue is purified by CC on silica gel with EtOAc/hexane
  9. customEvaporation of appropriate fractions

Sources & evidence

ORD record
ord-c11f2d58b0d54df8861c432044f5399e
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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