4-Chlorofuro[3,2-c]pyridine → Furo[3,2-c]pyridine

HRID 2389866Notes

Reaction equation

HRID 2389866 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][N:3]=1>C(O)(=O)C.[Zn]>[O:10]1[C:6]2[CH:5]=[CH:4][N:3]=[CH:2][C:7]=2[CH:8]=[CH:9]1

Participants

4

Reactant 1

HCID 27797464-Chlorofuro[3,2-c]pyridine

Product 1

HCID 12234604Furo[3,2-c]pyridineYield 73.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4-chlorofuro[3,2-c]pyridine (10.0 g, 65.1 mmol) in acetic acid (130 mL) was added zinc (10.0 g, 153 mmol), and the mixture was heated under reflux for 2 hr and filtered. The filtrate was concentrated under reduced pressure. The residue was basified with 1M aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (5.67 g, yield 73%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-61671042ded04dc7a5dd3ea2eec085f2
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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