Iodine → 2-Iodo-5-[2-{3-pyridyl}ethenyl]furan

HRID 52170Notes

Reaction equation

HRID 52170 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=1.C([N-]C(C)C)(C)C.[Li+].[I:22]I>C1COCC1>[I:22][C:11]1[O:10][C:9]([CH:8]=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 545597812-[2-{3-Pyridyl}ethenyl]furan

Product 1

HCID 545240982-Iodo-5-[2-{3-pyridyl}ethenyl]furanYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred -78° C. solution of 2-[2-{3-pyridyl}ethenyl]furan (0.95 g, 5.5 mmol), prepared as in step 4, in THF (25 mL) was added lithium diisopropylamide (4 mL, 6 mmol, 1.5M in hexanes). The cold reaction mixture was stirred 1 hour, followed by the addition of a THF (3 mL) solution of iodine (1.39 g, 5.5 mmol). The ice bath was removed and the reaction mixture allowed to stir at ambient temperature overnight. Saturated NH4Cl was added and the mixture diluted with ether. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel eluting with 40% ethyl acetate-hexanes to afford 1.1 g of 2-iodo-5-[2-{3-pyridyl}ethenyl]furan.

Workup

  1. customThe cold reaction mixture
  2. customThe ice bath was removed
  3. stirringto stir at ambient temperature overnight
  4. additionSaturated NH4Cl was added
  5. additionthe mixture diluted with ether
  6. washThe organic layer was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by column chromatography on silica gel eluting with 40% ethyl acetate-hexanes

Sources & evidence

ORD record
ord-56245be6e4404a74abe99bad5e4524e8
Source dataset
uspto-grants-1997_04
Patent number
US05616596

Reaction notes

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