m-Chloroperbenzoic acid → 2-(Trimethylsilyl)furo[3,2-B]pyridine 4-oxide

HRID 1042852Notes

Reaction equation

HRID 1042852 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[O:11][C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:22])C=1>C(Cl)Cl>[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[O:11][C:10]2[C:5](=[N+:6]([O-:22])[CH:7]=[CH:8][CH:9]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 136365392-(Trimethylsilyl)furo[3,2-b]pyridine

Product 1

HCID 667793722-(Trimethylsilyl)furo[3,2-B]pyridine 4-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-(Trimethylsilyl)furo[3,2-b]pyridine (14.68 g, 76.7 mmol) was dissolved in 80 mL DCM and cooled to 0° C. m-CPBA (33.1 g, 192 mmol) was dissolved in 160 mL DCM and slowly added to the reaction vessel. Upon complete addition, the reaction was warmed to RT and stirred for three hours. Reaction was diluted with DCM and washed twice with saturated sodium bicarbonate solution. 30 g of carbonate scavenger beads (˜30 mmol) were added to the organic layer and the solution was stirred for 30 minutes. The reaction was filtered, washed with brine, dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (gradient elution 0-10% MeOH:DCM) to afford 2-(trimethylsilyl)furo[3,2-b]pyridine N-oxide as a light brown oil that solidified under high vacuum. MS: M+H+=208.2

Workup

  1. additionslowly added to the reaction vessel
  2. additionUpon complete addition
  3. customReaction
  4. washwashed twice with saturated sodium bicarbonate solution
  5. addition30 g of carbonate scavenger beads (˜30 mmol) were added to the organic layer
  6. stirringthe solution was stirred for 30 minutes
  7. filtrationThe reaction was filtered
  8. washwashed with brine
  9. dry with materialdried with sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe material was purified via column chromatography (gradient elution 0-10% MeOH:DCM)

Sources & evidence

ORD record
ord-740000ac94694e9e89f6ed7227aa1903
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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