Hydrochloric Acid → 2-[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy)-3-pyridyl]acetic acid

HRID 1294265Notes

Reaction equation

HRID 1294265 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:31]=[CH:30][C:18]([CH2:19][O:20][C:21]2[C:26]([CH2:27][C:28]#N)=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:17][CH:16]=1.O1CCCC1.[OH-:37].[Na+].Cl.[OH2:40]>C(O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20][C:21]2[C:26]([CH2:27][C:28]([OH:40])=[O:37])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 688841392-[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile

Product 1

HCID 99105492-[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy)-3-pyridyl]acetic acidYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile (0.20 g), tetrahydrofuran (0.5 mL) and ethanol (1 mL) was added a 2N aqueous sodium hydroxide solution (1.5 mL) and the mixture was stirred with heating under reflux for 10 hrs. 1N Hydrochloric acid (3 mL) and water were added to the reaction mixture, the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (0.08 g, 38%) of 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetic acid from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 144-145° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 10 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-91380ad63c6d40959bd145a8c4629292
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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