Pyridine → HCID 57940892, compound

HRID 1437476Notes

Reaction equation

HRID 1437476 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](/[CH:10]=[CH:11]/[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:7][C:6]=2[CH:18]=1.[CH:19]1[C:24]([OH:25])=[CH:23][CH:22]=[C:21]([CH3:26])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1>O>[CH3:26][C:21]1[CH:20]=[CH:19][C:24]([O:25][C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8](/[CH:10]=[CH:11]/[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[N:7][C:6]=3[CH:18]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 2879P-CresolHCID 11430Potassium CarbonateHCID 68893999HCID 68893999, compound

Product 1

HCID 57940892HCID 57940892, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

Under an argon stream, a mixture of 5-bromo-2-[(E)-2-phenylethenyl]benzoxazole (Compound of Reference Example 43) (105 mg), p-cresol (45 mg), potassium carbonate (97 mg), copper oxide(II) (70 mg) and pyridine (1.5 ml) was stirred at 130° C. for 24 hours. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with a 5% aqueous solution of potassium hydrogen sulfate and water and dried over MgSO4. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography. The fraction eluted with ethyl acetate-hexane (1:6, v/v) was concentrated under reduced pressure, and the resulting crystals were collected by filtration to obtain 5-(4-methylphenoxy)-2-[(E)-2-phenylethenyl]benzoxazole (69 mg, 60%). The compound was recrystallized from ethyl acetate-hexane.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a 5% aqueous solution of potassium hydrogen sulfate and water
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was distilled off under reduced pressure
  5. washThe fraction eluted with ethyl acetate-hexane (1:6, v/v)
  6. concentrationwas concentrated under reduced pressure
  7. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-1326953679ab495ca410d2fd29959882
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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