Hydrochloric Acid → HCID 69215689, compound

HRID 2221794Notes

Reaction equation

HRID 2221794 reaction equation
[C:1]1([C:7]2[O:8][C:9]([CH3:40])=[C:10]([CH2:12][O:13][C:14]3[CH:39]=[CH:38][C:17]([CH2:18][O:19][C:20]4[C:24](/[CH:25]=[CH:26]/[C:27]([O:29]CC)=[O:28])=[CH:23][N:22]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[N:21]=4)=[CH:16][CH:15]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.[OH-].[Na+].Cl>O.C(O)C>[C:1]1([C:7]2[O:8][C:9]([CH3:40])=[C:10]([CH2:12][O:13][C:14]3[CH:39]=[CH:38][C:17]([CH2:18][O:19][C:20]4[C:24](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:23][N:22]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[N:21]=4)=[CH:16][CH:15]=3)[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86605778HCID 86605778, compound

Product 1

HCID 69215689HCID 69215689, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of ethyl (2E)-3-[3-({4-[(2-phenyl-5-methyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)-1-phenyl-1H-pyrazol-4-yl]-2-propenoate (0.39 g), tetrahydrofuran (3 mL) and ethanol (3 mL) was added 1N aqueous sodium hydroxide solution (3 mL), and the mixture was heated under reflux for 2 hrs. The reaction mixture was neutralized by adding 1N hydrochloric acid and water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give (2E)-3-[3-({4-[(2-phenyl-5-methyl-1,3-oxazol-4-yl)methoxy]benzyl}oxy)-1-phenyl-1H-pyrazol-4-yl]-2-propenoic acid as colorless crystals (0.32 g, yield 86%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 186-187° C.

Workup

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

Sources & evidence

ORD record
ord-700260d4d6e74a168254ff08ac3e8287
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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