m-Chloroperbenzoic acid → Furo[3,2-b]pyridine 4-oxide

HRID 1192402Notes

Reaction equation

HRID 1192402 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]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12210217Furo(3,2-b)pyridine

Product 1

HCID 10630536Furo[3,2-b]pyridine 4-oxideYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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

  1. filtrationThen the mixture was filtered through a alumina (140 g, basic)
  2. 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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