m-Chloroperbenzoic acid → HCID 21083624, compound

HRID 347696Notes

Reaction equation

HRID 347696 reaction equation
[CH2:1]([Sn:5]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:12][CH2:13][CH2:14][CH3:15])[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].ClC1C=C(C=CC=1)C(OO)=[O:25]>C(Cl)(Cl)Cl>[CH2:16]([Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:12][CH2:13][CH2:14][CH3:15])[C:6]1[CH:11]=[CH:10][N+:9]([O-:25])=[CH:8][CH:7]=1)[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 27373184-(Tri-n-butylstannyl)pyridine

Product 1

HCID 21083624HCID 21083624, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Tributylstannylpyridine (3.00 g, 8.15 mmol) and 3-chloroperoxybenzoic acid (2.81 g, 16.3 mmol) in CHCl3 (60 ml) was stirred at 0° C. for 24 h. The mixture was washed with saturated aqueous NaHCO3 (2×200 ml). The organic layer was dried (Na2SO4), filtered, and evaporated in vacuo. Purification by chromatography (silica gel, 0–10% MeOH/EtOAc) gave 2.00 g (64%) of the title compound: 1H NMR (360 MHz, CDCl3) δ 0.80–1.60 (27H, m), 7.42 (2H, d, J 5.0), 8.35 (2H, d, J 5.0).

Workup

  1. washThe mixture was washed with saturated aqueous NaHCO3 (2×200 ml)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customPurification by chromatography (silica gel, 0–10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-202de8cc7a6349c496e6d0b003e5f6d5
Source dataset
uspto-grants-2007_02
Patent number
US07176203B2

Reaction notes

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