Sodium Iodide → HCID 57516641, compound

HRID 1898607Notes

Reaction equation

HRID 1898607 reaction equation
[I-:1].[Na+].Cl[C:4]1[CH:9]=[C:8]([C:10]2[CH2:14][CH2:13][CH2:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1.C(Cl)(=O)C>C(#N)C>[I:1][C:4]1[CH:9]=[C:8]([C:10]2[CH2:14][CH2:13][CH2:12][CH:11]=2)[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 57516640HCID 57516640, compound

Product 1

HCID 57516641HCID 57516641, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A flask was charged with sodium iodide (3.75 g, 25.0 mmol), 2-chloro-4-cyclopent-1-enyl-pyridine (450 mg, 2.5 mmol) and acetonitrile (8 mL). Acetyl chloride (0.27 mL, 3.76 mmol) was slowly added and the reaction mixture was heated at reflux overnight. The reaction mixture was cooled to room temperature and quenched with water. Saturated Na2CO3 and 10% Na2S2O3 were added and the mixture was extracted with EtOAc (3×). The combined organics were dried over MgSO4 and concentrated. The residue was purified by chromatography (0% to 10% EtOAc/hexanes) to afford 2-iodo-4-cyclopent-1-enyl-pyridine as a white solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customquenched with water
  4. additionSaturated Na2CO3 and 10% Na2S2O3 were added
  5. extractionthe mixture was extracted with EtOAc (3×)
  6. dry with materialThe combined organics were dried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (0% to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8f8715c57c7147dca50d4a5f6e0781a3
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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