Hydrochloric Acid → HCID 10224612, compound

HRID 1294340Notes

Reaction equation

HRID 1294340 reaction equation
[CH3:1][C:2]1OC(C2C=CC=CC=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:31]=[CH:30][C:18]([O:19][CH2:20][C:21]2[C:26]([CH2:27][C:28]#N)=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:17][CH:16]=1.[CH2:32]([OH:34])[CH3:33].[OH-:35].[Na+].Cl.[OH2:38]>>[CH3:1][C:2]1[O:34][C:32]([C:33]2[CH:30]=[CH:31][CH:15]=[CH:16][CH:17]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][C:21]2[C:26]([CH2:27][C:28]([OH:38])=[O:35])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:30][CH:31]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 68887664HCID 68887664, compound

Product 1

HCID 10224612HCID 10224612, compoundYield 86%

Procedure

To a mixture of 2-[2-[[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenoxy]methyl]-3-pyridyl]acetonitrile (1.19 g) and ethanol (15 mL) was added a 2N aqueous sodium hydroxide solution (15 mL) and the mixture was heated under reflux for 5 hrs. 1N Hydrochloric acid (30 mL) and water were added to 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 (1.08 g, 86%) of 2-[2-[[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenoxy]methyl]-3-pyridyl]acetic acid. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 126-127° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 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-f39b3087227f40f38eeb0e7915e423e1
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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