m-Chloroperbenzoic acid → Furo[3,2-b]pyridine 4-oxide
Reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C1C=C(Cl)C=C(C(OO)=[O:18])C=1>C(Cl)(Cl)Cl>[O:1]1[C:9]2[C:4](=[N+:5]([O-:18])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of Furo[3,2-b]pyridine (1.5 g, 13.0 mmol) in CHCl3 (30 mL) was added MCPBA (2.9 g, 17.0 mmol). The mixture was stirred at room temperature for 16 hours. Then the mixture was filtered through a alumina (140 g, basic) and washed with ethyl acetate/hexane (1:1) and DCM/MeOH (20:1) to give Furo[3,2-b]pyridine 4-oxide (1.49 g, 88%). 1H NMR (CDCl3, 400 MHz) δ 8.25 (m, 1H), 7.81 (m, 1H), 7.51 (m, 1H), 7.23 (m, 1H).
Workup
- filtrationThen the mixture was filtered through a alumina (140 g, basic)
- washwashed with ethyl acetate/hexane (1:1) and DCM/MeOH (20:1)
Sources & evidence
- ORD record
- ord-9f3a2bcc15604a0da768bf3018928a71
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680114B2
Reaction notes
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