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

HRID 233272Notes

Reaction equation

HRID 233272 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].[H-].[Na+].O>C1COCC1>[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 4

HCID 962WaterHCID 24758Sodium hydrideHCID 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 1

HCID 8028TetrahydrofuranSolvent

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) was added, in small portions, sodium hydride (60% in oil, 6.92 g), and the mixture was stirred. The reaction mixture was stirred, at room temperature, for further 15 hours, which was poured into water, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure. The residual crystals are collected by filtration, followed by recrystallization from ethanol to afford 2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]-5-nitropyridine (25.4 g, 49%) as yellowish brown crystals, m.p.110.5°-111.5° C.

Workup

  1. stirringThe reaction mixture was stirred, at room temperature, for further 15 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off under reduced pressure
  6. filtrationThe residual crystals are collected by filtration
  7. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-30b952e022344b0dbad2af6c1d90e27d
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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