Water → Methyl 2-(5-methyl-2-phenyl-4-oxazolyl)methoxy-4-pyridinecarboxylate

HRID 349947Notes

Reaction equation

HRID 349947 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][OH:16].Cl[C:18]1[CH:23]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20][N:19]=1.O>CN(C)C=O.O1CCCC1>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][O:16][C:18]1[CH:23]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20][N:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 115719324-(Hydroxymethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 17861336Methyl 2-(5-methyl-2-phenyl-4-oxazolyl)methoxy-4-pyridinecarboxylateYield 14%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride-(60%, oily, 2.40 g) was added to a solution of 5-methyl-2-phenyl-4-oxazolylmethanol (9.46 g) in N,N-dimethylformamide (50 ml) at 0° C., which was stirred for 15 minutes. A solution of methyl 2-chloro-4-pyridinecarboxylate (8.58 g) in tetrahydrofuran (50 ml) was added to the mixture. After being stirred at room temperature for 1 hour, the reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography to obtain methyl 2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridinecarboxylate (2190 mg, yield 14%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 106–107° C.

Workup

  1. stirringAfter being stirred at room temperature for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f7da6c55187484d93df9763bcc960b9
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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