m-Chloroperbenzoic acid → 3-(Methoxyimino)-2,3-dihydrofuro[2,3-c]pyridine 6-oxide

HRID 1508212Notes

Reaction equation

HRID 1508212 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][N:9]=[CH:10][CH:11]=2)[O:6][CH2:5]1.ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][N+:9]([O-:21])=[CH:10][CH:11]=2)[O:6][CH2:5]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86721903furo[2,3-c]pyridin-3(2H)-one O-methyl oxime

Product 1

HCID 867219123-(Methoxyimino)-2,3-dihydrofuro[2,3-c]pyridine 6-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of furo[2,3-c]pyridin-3(2H)-one O-methyl oxime (5.35 mmol) (A.2.4.4) in 15 mL DCM was added 3-chloroperbenzoic acid (16.0 mmol). The mixture was stirred at RT overnight, diluted with 20 mL DCM and extracted with sat. aq. NaHCO3 solution (2×), with sat. aq. Na2S2O3 solution (2×) and brine. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as yellow solid;

Workup

  1. extractionextracted with sat. aq. NaHCO3 solution (2×), with sat. aq. Na2S2O3 solution (2×) and brine
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0feeeed9baa4ec598464f76a60c818c
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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