Hydrochloric Acid → HCID 68889489, compound

HRID 1294315Notes

Reaction equation

HRID 1294315 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:30])=[C:9]([CH2:11][O:12][C:13]2[CH:29]=[CH:28][C:16]([CH2:17][O:18][C:19]3[C:24]([CH2:25][C:26]#N)=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:15][CH:14]=2)[N:10]=1.COCCO.[OH-:36].[K+].Cl.[OH2:39]>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:30])=[C:9]([CH2:11][O:12][C:13]2[CH:29]=[CH:28][C:16]([CH2:17][O:18][C:19]3[C:24]([CH2:25][C:26]([OH:39])=[O:36])=[CH:23][CH:22]=[CH:21][N:20]=3)=[CH:15][CH:14]=2)[N:10]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 80192-MethoxyethanolHCID 14797Potassium HydroxideHCID 68886299HCID 68886299, compound

Product 1

HCID 68889489HCID 68889489, compoundYield 63%

Procedure

To a mixture of 2-[2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]benzyloxy]-3-pyridyl]acetonitrile (0.60 g) and 2-methoxyethanol (2 mL) was added a 4N aqueous potassium hydroxide solution (2 mL) and the mixture was heated under reflux for 4 hrs. 1N Hydrochloric acid (8 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 (0.40 g, 63%) of 2-[2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]benzyloxy]-3-pyridyl]acetic acid. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 151-152° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 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-8f444f7447e147dbb6937c40278a0ee0
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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