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

HRID 1294138Notes

Reaction equation

HRID 1294138 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][OH:14].[H-].[Na+].[H][H].Cl[C:20]1[CH:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][N:21]=1>O1CCCC1.O.CN(C)C=O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:20]1[CH:25]=[C:24]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=[CH:22][N:21]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 115719324-(Hydroxymethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 17861336Methyl 2-(5-methyl-2-phenyl-4-oxazolyl)methoxy-4-pyridinecarboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (5-methyl-2-phenyl-4-oxazolyl)methanol (9.46 g) and N,N-dimethylformamide (0.50 mL) was added sodium hydride (60%, oil, 2.40 g) at room temperature and the reaction mixture was stirred at room temperature until generation of hydrogen ended. The mixture was added to a solution of methyl 2-chloropyridine-4-carboxylate (8.58 g) in tetrahydrofuran (50 ml) at room temperature and the resulting mixture was further stirred at room temperature for 1 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals of methyl 2-(5-methyl-2-phenyl-4-oxazolyl)methoxy-4-pyridinecarboxylate from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless needle crystals (2.19 g, 14%). melting point: 106-107° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a23827540a384970a238081ffc7fd16f
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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