Tetrahydrofuran → HCID 68885136, compound

HRID 1294351Notes

Reaction equation

HRID 1294351 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:16]=[C:17]([CH:38]=[CH:39][CH:40]=1)[CH2:18][S:19][C:20]1[CH:21]=[C:22]([CH:35]=[CH:36][CH:37]=1)[CH2:23][CH:24](C(OCC)=O)[C:25]([O:27]CC)=[O:26].[OH-].[K+].O1CCCC1>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]=[C:17]([CH:38]=[CH:39][CH:40]=1)[CH2:18][S:19][C:20]1[CH:21]=[C:22]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])[CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 68883930HCID 68883930, compound

Product 1

HCID 68885136HCID 68885136, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl 2-[3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]benzyl]malonate (0.70 g), a 4N aqueous potassium hydroxide solution (10 mL), tetrahydrofuran (20 mL) and ethanol (20 mL) was stirred at 60° C. for 1 hr. The reaction mixture was concentrated and water was added to the residue. The mixture was neutralized with 2N hydrochloric acid, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in pyridine (40 mL) and this mixture was stirred with heating under reflux for 1 hr. The reaction mixture was concentrated, 2N hydrochloric acid was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated to give crystals (0.44 g, yield 77%) of 3-[3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]phenyl]propionic acid. Recrystallization from acetone-hexane gave colorless prism crystals. melting point: 120-121° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added to the residue
  3. filtrationthe precipitated crystals were collected by filtration
  4. dissolutionThe obtained crystals were dissolved in pyridine (40 mL)
  5. temperaturewith heating
  6. temperatureunder reflux for 1 hr
  7. concentrationThe reaction mixture was concentrated
  8. addition2N hydrochloric acid was added to the mixture
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-1de23cffc19241ec88a0767a1ca21c1f
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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