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

HRID 2168153Notes

Reaction equation

HRID 2168153 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.ClC1C=CC=C(C(OO)=[O:22])C=1>ClCCl>[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 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

2-Trimethylsilanyl-furo[3,2-b]pyridine (268 g, 0.14 mol) is dissolved in dichloromethane (3 l) and stirred at 0-5° C. To the solution is added 3-chloroperbenzoic acid over 30 min, stirred 1 h and warmed up to room temperature. After 14 h the reaction mixture is extracted with NaHCO3 solution and water. The organic layer is separated and dried over Na2SO4. The drying agent is filtered and the solvent is removed in vacuum; yield: 296 g 2-trimethylsilanyl-furo[3,2-b]pyridine 4-oxide; HPLC/MS: 2.0 min, [M+H]=208;

Workup

  1. stirringstirred 1 h
  2. temperaturewarmed up to room temperature
  3. extractionAfter 14 h the reaction mixture is extracted with NaHCO3 solution and water
  4. customThe organic layer is separated
  5. dry with materialdried over Na2SO4
  6. filtrationThe drying agent is filtered
  7. customthe solvent is removed in vacuum
  8. custom2.0 min, [M+H]=208

Sources & evidence

ORD record
ord-052b2e5a3baa48fe8dabf770874ca4bc
Source dataset
uspto-grants-2015_06
Patent number
US09045493B2

Reaction notes

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