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

HRID 1295227Notes

Reaction equation

HRID 1295227 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+].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>[CH3:1][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: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

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

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-75302d8cf1a74456b7e7fc34605b090d
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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