Water → Methyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolecarboxylate

HRID 1294153Notes

Reaction equation

HRID 1294153 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.[H-].[Na+].Cl[CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20].O>CN(C)C=O>[CH3:20][C:19]1[O:18][C:17]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[N:16][C:15]=1[CH2:14][O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 178498603HCID 178498603, compound

Product 1

HCID 17861331Methyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolecarboxylateYield 72.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-hydroxyisoxazole-5-carboxylate (5.01 g) in N,N-dimethylformamide (70 mL) was added sodium hydride (60%, oil, 1.40 g) at 0° C. and, after stirring the mixture for 15 min., 4-chloromethyl-5-methyl-2-phenyloxazole (7.26 g) was added. After stirring the mixture at 60° C. for 2 hrs., the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolecarboxylate (7.96 g, yield 72%) as colorless crystals from a fraction eluted with tetrahydrofuran-hexane (1:1, v/v). The crystals were recrystallized from tetrahydrofuran-hexane. melting point: 123-124° C.

Workup

  1. stirringAfter stirring the mixture at 60° C. for 2 hrs
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a65fdb30fb254a68b28b44b8d59fc4dc
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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