Water → 2-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy)-5-nitropyridine

HRID 2395695Notes

Reaction equation

HRID 2395695 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][C:12]1[O:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][C:13]=1[CH2:23][CH2:24][OH:25].O>C1COCC1.[H-].[Na+]>[CH3:11][C:12]1[O:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:14][C:13]=1[CH2:23][CH2:24][O:25][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 783082-Chloro-5-nitropyridineHCID 7255852-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

Product 1

HCID 110673292-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy)-5-nitropyridineYield 49.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24758Sodium hydrideSolvent

Procedure

To a solution of 2-chloro-5-nitropyridine (25 g) and 2-(5-methyl-2-phenyl-4-oxazolyl)ethanol (32.1 g) in THF (250 ml), sodium hydride in oil (60%, 6.92 g) was added gradually while the solution was stirred under ice cooling conditions. The reaction mixture was stirred at room temperature for 15 more hours, after which it was added to water and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure. The residual crystal was collected by filtration and recrystallized from ethanol to yield 2-[2-(5-methyl-2-phenyl-4-oxazolyl]ethoxy]-5-nitropyridine (25.4 g, 49%) as a yellow-brown crystal.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 15 more hours
  2. extractionextracted with ethyl acetate
  3. washAfter the ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off under reduced pressure
  6. filtrationThe residual crystal was collected by filtration
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5eeeed38444b49b88ef74271c3f8c96b
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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