Hydrochloric Acid → 2-[5-Hydroxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetic acid

HRID 1294247Notes

Reaction equation

HRID 1294247 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[N:22]=[C:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:24][C:25]=3[CH3:26])=[CH:15][CH:14]=2)=[C:6](CC#N)[CH:7]=1.[CH2:33]([OH:35])[CH3:34].[OH-:36].[K+].Cl>O>[OH:35][C:33]1[CH:7]=[CH:6][C:5]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]3[N:22]=[C:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[O:24][C:25]=3[CH3:26])=[CH:17][CH:18]=2)=[C:4]([CH2:3][C:2]([OH:1])=[O:36])[CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 688862422-[5-Hydroxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetonitrile

Product 1

HCID 688848412-[5-Hydroxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetic acidYield 16%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-[5-hydroxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetonitrile (0.30 g) and ethanol (3 mL) was added a 4N aqueous potassium hydroxide solution (1 mL) and the mixture was stirred with heating under reflux for 24 hrs. 1N Hydrochloric acid and water were added to acidify the reaction mixture, and the mixture was extracted with ethyl acetate-tetrahydrofuran. 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 (0.05 g, 16%) of 2-[5-hydroxy-2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetic acid from a fraction eluted with ethyl acetate-hexane (5:1, v/v). Recrystallization from tetrahydrofuran-hexane gave pale-brown prism crystals. melting point: 194-195° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 24 hrs
  3. extractionthe mixture was extracted with ethyl acetate-tetrahydrofuran
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-003154ad4949477d8766f775c2dfe705
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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