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

HRID 1267312Notes

Reaction equation

HRID 1267312 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 stirred solution of 2-chloro-5-nitropyridine (25 g), 2-(5-methyl-2-phenyl-4-oxazolyl)ethanol (32.1 g) in THF (250 ml) was added portionwise, under ice-cooling, sodium hydride (60% in oil, 6.92 g). The reaction mixture was stirred for further 15 hours at room temperature, which was poured into water, followed by extraction with ethyl acetate. The ethyl acetate was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure. The residual crystals were collected by filtration. Recrystallization from ethanol gave 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. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe ethyl acetate was washed with water
  4. dry with materialdried (MgSO4)
  5. distillationthe solvent was distilled off under reduced pressure
  6. filtrationThe residual crystals were collected by filtration
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-ad90e485b2f94eb1b9ca6d301b1f9836
Source dataset
uspto-grants-2003_04
Patent number
US06552058B1

Reaction notes

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