m-Chloroperbenzoic acid → HCID 17861268, compound

HRID 1294198Notes

Reaction equation

HRID 1294198 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>[C:29]([O:31][CH2:1][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)(=[O:30])[CH3:25]

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 overnight at room temperature and concentrated. The residue was subjected to silica gel column chromatography to give a colorless oil from a fraction eluted with tetrahydrofuran. A solution of the obtained colorless oil in acetic anhydride (100 mL) was slowly added to acetic anhydride (200 mL) heated to 130° C. and the mixture was stirred for 2 hrs. and concentrated. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium hydrogencarbonate and then with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to give [5-(5-methyl-2-phenyl-4-oxazolylmethoxy)-2-pyridylmethyl] acetate (18.09 g, yield 83%) as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

Workup

  1. concentrationconcentrated
  2. customto give a colorless oil from a fraction
  3. washeluted with tetrahydrofuran
  4. additionA solution of the obtained colorless oil in acetic anhydride (100 mL) was slowly added to acetic anhydride (200 mL)
  5. temperatureheated to 130° C.
  6. stirringthe mixture was stirred for 2 hrs
  7. concentrationand concentrated
  8. dissolutionThe residue was dissolved in ethyl acetate
  9. washwashed with saturated aqueous sodium hydrogencarbonate
  10. dry with materialwith saturated brine, dried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-c8af46d1935743f3a12f4248587bbacc
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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