2-Chlorofuro[3,2-b]pyridine → Furo(3,2-b)pyridine

HRID 2116802Notes

Reaction equation

HRID 2116802 reaction equation
Cl[C:2]1[O:10][C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[CH:3]=1>C(O)(=O)C.[Zn]>[O:10]1[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[CH:3]=[CH:2]1

Participants

4

Reactant 1

HCID 107255602-Chlorofuro[3,2-b]pyridine

Product 1

HCID 12210217Furo(3,2-b)pyridine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Chlorofuropyridine (7, 1.27 g, 8.27 mmol) is treated with zinc (3.23 g, 49.6 mmol) in acetic acid (20 ml) at refluxing temperature until the starting material disappears (˜4 hours). The reaction is filtered to remove solid. The filtrate is concentrated and the residue is dissolved in water. After basification with 1N sodium hydroxide, the mixture is extracted with methylene chloride. Evaporation leaves a yellow oil, which is purified with flash column chromatography on silica gel to give furopyridine as a yellow oil (8).

Workup

  1. temperatureat refluxing temperature until the starting material
  2. custom(˜4 hours)
  3. filtrationThe reaction is filtered
  4. customto remove solid
  5. concentrationThe filtrate is concentrated
  6. dissolutionthe residue is dissolved in water
  7. extractionAfter basification with 1N sodium hydroxide, the mixture is extracted with methylene chloride
  8. customEvaporation
  9. customleaves a yellow oil, which
  10. customis purified with flash column chromatography on silica gel

Sources & evidence

ORD record
ord-3de1c72e4e3e429ea0e5e5f6958e7d84
Source dataset
uspto-grants-2008_10
Patent number
US07439374B2

Reaction notes

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