alpha-(5-Ethyl-2-methoxy-6-methyl-3-pyridinyl)-2-benzoxazoleethanol → 3-[2-(benzoxazol-2-yl)ethenyl]-5-ethyl-6-methyl-2-(1H)-pyridinone

HRID 273682Notes

Reaction equation

HRID 273682 reaction equation
O[CH:2]([C:13]1[C:14]([O:22]C)=[N:15][C:16]([CH3:21])=[C:17]([CH2:19][CH3:20])[CH:18]=1)[CH2:3][C:4]1[O:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.Cl.N1C=CC=CC=1>>[O:5]1[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=[C:4]1[CH:3]=[CH:2][C:13]1[C:14](=[O:22])[NH:15][C:16]([CH3:21])=[C:17]([CH2:19][CH3:20])[CH:18]=1

Participants

3

Reactant 2

HCID 10064107alpha-(5-Ethyl-2-methoxy-6-methyl-3-pyridinyl)-2-benzoxazoleethanolHCID 10176127Pyridinium chloride

Product 1

HCID 4548263-[2-(benzoxazol-2-yl)ethenyl]-5-ethyl-6-methyl-2-(1H)-pyridinoneYield 76%

Procedure

A mixture of 2-[2(R/S)-hydroxy-2-(2-methoxy-5-ethyl-6-methylpyridin-3-yl)ethyl]benzoxazole (72 mg, 0.23 mmol) and pyridine hydrochloride (133 mg, 1.2 mmol), under a nitrogen atmosphere, was placed in a preheated oil bath (165° C.) for 5 minutes. The reaction flask was removed, cooled, and water added to give a solid. This crude product was extracted into chloroform, dried (MgSO4) and the solvent evaporated to yield 49 mg (75%) of pure product. Recrystallization from methanol gave 15 mg of analytically pure product, mp 262°-264° C.

Workup

  1. customunder a nitrogen atmosphere, was placed in a preheated oil bath
  2. customThe reaction flask was removed
  3. temperaturecooled
  4. additionwater added
  5. customto give a solid
  6. extractionThis crude product was extracted into chloroform
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-2b4dd72fbcbd4e048059116a59401279
Source dataset
uspto-grants-1995_02
Patent number
US05387512

Reaction notes

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