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 2081532Notes

Reaction equation

HRID 2081532 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)-pyridinone

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 pure product. Recrystallization from methanol gave 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
  9. customto yield pure product
  10. customRecrystallization from methanol
  11. customgave analytically pure product, mp 262°-264° C.

Sources & evidence

ORD record
ord-50b252b847f14c71aedfd04fcfcee997
Source dataset
uspto-grants-1993_02
Patent number
US05185251

Reaction notes

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