Dimethylformamide → HCID 68887611, compound

HRID 1294296Notes

Reaction equation

HRID 1294296 reaction equation
Cl[CH2:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[O:5][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:10][C:11]=1[CH3:12].[OH:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:33]C)=[O:32])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:12][C:11]1[O:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][C:7]=1[CH2:6][O:5][C:4]1[CH:19]=[CH:20][CH:21]=[CH:22][C:3]=1[CH2:2][O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:30][C:31]([OH:33])=[O:32])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl esterHCID 110990364-(2-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole

Product 1

HCID 68887611HCID 68887611, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(2-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (0.98 g), methyl 2-(4-hydroxyphenyl)acetate (0.51 g), anhydrous potassium carbonate (0.52 g), and N,N-dimethylformamide (10 mL) was stirred at room temperature for 3 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with dilute hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give an oil from a fraction eluted with ethyl acetate-hexane (1:4, v/v). To a mixture of the obtained oil, tetrahydrofuran (6 mL), and methanol (6 mL) was added a 1N aqueous sodium hydroxide solution (6 mL) and the mixture was stirred at room temperature for 2 hrs. Dilute hydrochloric acid was added to acidify the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crystals (1.00 g, 76%) of 2-[4-[2-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetic acid. Recrystallization from acetone-hexane gave colorless prism crystals. melting point: 173-174° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with dilute hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil from a fraction
  6. washeluted with ethyl acetate-hexane (1:4, v/v)
  7. additionTo a mixture of the obtained oil, tetrahydrofuran (6 mL), and methanol (6 mL)
  8. additionwas added a 1N aqueous sodium hydroxide solution (6 mL)
  9. stirringthe mixture was stirred at room temperature for 2 hrs
  10. additionDilute hydrochloric acid was added
  11. extractionthe mixture was extracted with ethyl acetate
  12. washThe organic layer was washed with saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-ab62dfce197f4b0eb461351442d1b011
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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