m-Chloroperbenzoic acid → HCID 17861268, compound

HRID 349979Notes

Reaction equation

HRID 349979 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[N:11]=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:13][C:14]=2[CH3:15])=[CH:4][N:3]=1.ClC1C=CC=[C:25]([C:29]([O:31]O)=[O:30])C=1>O1CCCC1>[CH3:15][C:14]1[O:13][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:11][C:10]=1[CH2:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][O:31][C:29](=[O:30])[CH3:25])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 17861255HCID 17861255, compound

Product 1

HCID 17861268HCID 17861268, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-methyl-5-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine (18.04 g), 3-chloroperbenzoic acid (18.85 g) and tetrahydrofuran (100 ml) was stirred at room temperature overnight, and concentrated. The residue was subjected to silica gel column chromatography to obtain a colorless oily substance from the fraction eluted with tetrahydrofuran. A solution of the obtained colorless oily substance in acetic anhydride (100 ml) was added slowly to acetic anhydride (200 ml) heated at 130° C., which was stirred for 2 hours, and concentrated. The residue was dissolved in ethyl acetate, which was washed with an aqueous saturated sodium bicarbonate solution, then with a saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to obtain [5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-pyridylmethyl]acetate (18.09 g, yield 83%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

Workup

  1. concentrationconcentrated
  2. customto obtain a colorless oily substance from the fraction
  3. washeluted with tetrahydrofuran
  4. additionA solution of the obtained colorless oily substance in acetic anhydride (100 ml) was added slowly to acetic anhydride (200 ml)
  5. temperatureheated at 130° C.
  6. stirringwhich was stirred for 2 hours
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. washwhich was washed with an aqueous saturated sodium bicarbonate solution
  10. dry with materialwith a saturated aqueous sodium chloride solution, dried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-c92d37f625a54da8a78e0c36d871ede7
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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