2-Chlorofuro[3,2-b]pyridine → Furo(3,2-b)pyridine
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]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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
- temperatureat refluxing temperature until the starting material
- custom(˜4 hours)
- filtrationThe reaction is filtered
- customto remove solid
- concentrationThe filtrate is concentrated
- dissolutionthe residue is dissolved in water
- extractionAfter basification with 1N sodium hydroxide, the mixture is extracted with methylene chloride
- customEvaporation
- customleaves a yellow oil, which
- 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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