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

HRID 1470335Notes

Reaction equation

HRID 1470335 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH3:12][Si:13]([CH3:24])([CH3:23])[C:14]1[O:22][C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=1>C(Cl)Cl>[CH3:12][Si:13]([CH3:24])([CH3:23])[C:14]1[O:22][C:21]2[C:16](=[N+:17]([O-:9])[CH:18]=[CH:19][CH:20]=2)[CH:15]=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

A solution of m-CPBA (17 g, 0.098 mmol) in DCM (80 ml) is added to a solution of 2-(Trimethylsilyl)furo(3,2-b)pyridine (7.5 g, 0.0392 mol) in dry DCM (50 ml) at 0° C. The reaction mixture is stirred at RT for 4 h and then diluted with DCM (100 ml), washed with saturated sodium bicarbonate (2×100 ml) and saturated brine (50 ml), dried over sodium sulphate and evaporated to afford the title compound as (6 g, 73.5%) light brown oil. TLC: chloroform/methanol (9/1): Rf=0.8; 1H NMR (DMSO-d6, 400 MHz) δ [ppm] 8.21-8.19 (1H, d, J1=6.4 Hz), 7.693-7.671 (1H, d, J1=8.52 Hz), 7.465-7.163 (1H, d, J1=1 Hz), 7.333-7.296 (1H, dd, J1=6.36 Hz, J2=8.48 Hz), 0.372-0.355 (9H, s).

Workup

  1. washwashed with saturated sodium bicarbonate (2×100 ml) and saturated brine (50 ml)
  2. dry with materialdried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-ba0d1492cc37489a946017616a955d79
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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