Dimethylformamide → Methyl 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate

HRID 2221627Notes

Reaction equation

HRID 2221627 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:24][C:25]1[N:26]=[C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:28][C:29]=1[CH3:30]>O>[CH3:30][C:29]1[O:28][C:27]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[N:26][C:25]=1[CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 11461459Methyl 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoateYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl 4-hydroxybenzoate (4.84 g), potassium carbonate (4.80 g), and N,N-dimethylformamide (50 mL) was added 4-(chloromethyl)-5-methyl-2-phenyl-1,3-oxazole (6.00 g) with stirring, and the mixture was stirred at 80° C. for 3 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with distilled water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate (8.09 g, yield 87%) from a fraction eluted with ethyl acetate-hexane (1:3, v/v). White crystals were obtained by recrystallization from ethyl acetate-diisopropyl ether. melting point: 104-105° C.

Workup

  1. stirringthe mixture was stirred at 80° C. for 3 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed successively with distilled water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4d70c5604fe647d1a78f82f6dadf70a8
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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