Methanol → Bmy 42393

HRID 257620Notes

Reaction equation

HRID 257620 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([O:27]C)=[O:26])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].CO>Cl>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([OH:27])=[O:26])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 10319549HCID 10319549, compound

Product 1

HCID 131961Bmy 42393Yield 80%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of methyl 2-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetate (2.25 g, 5.5 mmol), 3N sodium hydroxide solution (5.5 mL) and methanol (50 mL) was heated to reflux on a steam bath. After 5 minutes, the mixture was cooled, the methanol evaporated and the residue diluted with water. Warming provided a solution which was diluted with 1N hydrochloric acid solution to pH 3 to give an oily precipitate. The mixture was extracted with CH2Cl2 and the organic extracts washed twice with water and once with saturated sodium chloride solution. Concentration, after drying over sodium sulfate, left a pale yellow solid which was recrystallized twice from a mixture of hexanes and CH2Cl2 (2:1) to give 2-[3-[2-(4,5-diphenyl-2-oxazolyl)-ethyl]phenoxy]acetic acid (1.74 g, 80%), m.p. 153.3°-154.5° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux on a steam bath
  3. temperaturethe mixture was cooled
  4. customthe methanol evaporated
  5. additionthe residue diluted with water
  6. temperatureWarming
  7. customprovided a solution which
  8. customto give an oily precipitate
  9. extractionThe mixture was extracted with CH2Cl2
  10. washthe organic extracts washed twice with water and once with saturated sodium chloride solution
  11. concentrationConcentration
  12. dry with materialafter drying over sodium sulfate
  13. waitleft a pale yellow solid which
  14. customwas recrystallized twice from a mixture of hexanes and CH2Cl2 (2:1)

Sources & evidence

ORD record
ord-400836d2f6df463b9111887591735811
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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