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

HRID 2221623Notes

Reaction equation

HRID 2221623 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:27][C:28]1[N:29]=[C:30]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:31][C:32]=1[CH3:33]>O>[CH3:14][O:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[O:1][CH2:27][C:28]1[N:29]=[C:30]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:31][C:32]=1[CH3:33])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12038Ethyl vanillateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 69216123Ethyl 3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 4-hydroxy-3-methoxybenzoate (15.00 g), potassium carbonate (11.63 g) and N,N-dimethylformamide (2.00 mL) was added 4-chloromethyl-5-methyl-2-phenyl-1,3-oxazole (17.45 g) with stirring, and the mixture was stirred overnight at 80° C. Water was poured into the reaction mixture and 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 ethyl 3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave a pale-brown solid (25.45 g, yield 91%). melting point: 103-104° C.

Workup

  1. stirringthe mixture was stirred overnight at 80° C
  2. extractionextracted 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-e8af9029e5d54138a1a865eba54976dd
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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