Hydrochloric Acid → HCID 68884266, compound

HRID 1294266Notes

Reaction equation

HRID 1294266 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:22]([CH2:27][C:28]#[N:29])=N[CH:24]=[CH:25][CH:26]=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]([CH2:25][C:24]([OH:40])=[O:37])=[N:29][CH:28]=[CH:27][CH:22]=2)=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68885068HCID 68885068, compound

Product 1

HCID 68884266HCID 68884266, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-[3-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-2-pyridyl]acetonitrile (0.55 g), tetrahydrofuran (1 mL) and ethanol (4 mL) was added a 2N aqueous sodium hydroxide solution (4 mL) and the mixture was stirred with heating under reflux for 12 hrs. 1N Hydrochloric acid (8 mL) and water were added to the reaction mixture, and the precipitated solid was collected by filtration and dried with air to give crystals (0.35 g, 47%) of 2-[3-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-2-pyridyl]acetic acid. Recrystallization from tetrahydrofuran-hexane gave colorless prism crystals. melting point: 115-116° C. (dec.)

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 12 hrs
  3. filtrationthe precipitated solid was collected by filtration
  4. customdried with air

Sources & evidence

ORD record
ord-32d387940c2e43218117174e53f13033
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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