Hydrochloric Acid → HCID 68886166, compound

HRID 1294303Notes

Reaction equation

HRID 1294303 reaction equation
[CH3:1][C:2]1OC(C2C=CC=CC=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:29]=[CH:30][CH:31]=1)[CH2:18][O:19][C:20]1[CH:21]=[C:22]([CH2:26][C:27]#N)[CH:23]=[N:24][CH:25]=1.[OH-:32].[Na+].[CH2:34]([OH:36])[CH3:35].Cl.[OH2:38]>>[CH3:1][C:2]1[O:36][C:34]([C:35]2[CH:17]=[CH:16][CH:15]=[CH:31][CH:30]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:29]=[CH:30][CH:31]=1)[CH2:18][O:19][C:20]1[CH:21]=[C:22]([CH2:26][C:27]([OH:38])=[O:32])[CH:23]=[N:24][CH:25]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 68885115HCID 68885115, compound

Product 1

HCID 68886166HCID 68886166, compoundYield 85%

Procedure

A mixture of 2-[5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile (2.90 g), a 4N aqueous sodium hydroxide solution (15 mL) and ethanol (15 mL) was heated under reflux for 4 hrs. Water was added to the reaction mixture, and the reaction mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crystals (2.58 g, 85%) of 2-[5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetic acid. Recrystallization from tetrahydrofuran-hexane gave colorless prism crystals. melting point: 158-159° C.

Workup

  1. temperatureunder reflux for 4 hrs
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-be7b7fd6aaa8452db9fd4339de3b6dc2
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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