Dimethylformamide → Methyl 6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-carboxylate

HRID 2221527Notes

Reaction equation

HRID 2221527 reaction equation
[C:1]([C:9]1[CH:28]=[CH:27][C:12]([O:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[O:18][C:19]=2[CH3:20])=[CH:11][C:10]=1[OH:29])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:31][C:32]([O:34][CH3:35])=[O:33].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:20][C:19]1[O:18][C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:16][C:15]=1[CH2:14][O:13][C:12]1[CH:27]=[CH:28][C:9]2[C:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:31]([C:32]([O:34][CH3:35])=[O:33])[O:29][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 230766154-(4-Benzoyl-3-hydroxyphenoxymethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 69216315Methyl 6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(4-benzoyl-3-hydroxyphenoxymethyl)-5-methyl-2-phenyl-1,3-oxazole (54.93 g), methyl bromoacetate (32.88 g), potassium carbonate (19.76 g) and N,N-dimethylformamide (200 mL) was stirred at 90° C. for 15 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. A mixture of the obtained residue, 1,8-diazabicyclo[5.4.0]-7-undecene (21.77 g), and toluene (750 mL) was heated under reflux for 20 hrs with azeotropic removal of water. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:8, v/v) to give methyl 6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-carboxylate as colorless crystals (34.36 g, yield 55%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 139-140° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. additionA mixture of the obtained residue, 1,8-diazabicyclo[5.4.0]-7-undecene (21.77 g), and toluene (750 mL)
  6. temperaturewas heated
  7. temperatureunder reflux for 20 hrs with azeotropic removal of water
  8. concentrationThe reaction mixture was concentrated
  9. washeluted with ethyl acetate-hexane (1:8, v/v)

Sources & evidence

ORD record
ord-88ff7dfa634f426da606a03509aa1611
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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