Dimethylformamide → HCID 68883623, compound

HRID 1294295Notes

Reaction equation

HRID 1294295 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][CH2:7][C:8]1[N:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:11][C:12]=1[CH3:13].[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>[CH3:13][C:12]1[O:11][C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:9][C:8]=1[CH2:7][O:6][C:5]1[CH:4]=[C:3]([CH:22]=[CH:21][CH:20]=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 108815514-(3-Chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole

Product 1

HCID 68883623HCID 68883623, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-(3-chloromethylphenoxymethyl)-5-methyl-2-phenyloxazole (0.89 g), methyl 2-(4-hydroxyphenyl)acetate (0.50 g), anhydrous potassium carbonate (0.49 g) and N,N-dimethylformamide (15 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 colorless crystals from a fraction eluted with ethyl acetate-hexane (1:4, v/v). To a mixture of the obtained crystal, 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 (1.13 g, 93%) of 2-[4-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetic acid. Recrystallization from acetone-hexane gave colorless prism crystals. melting point: 179-180° 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 colorless crystals from a fraction
  6. washeluted with ethyl acetate-hexane (1:4, v/v)
  7. additionTo a mixture of the obtained crystal, 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-53fee977ba4c48a690df02b3af4dfcbb
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

Loading…