Sodium Hydroxide → HCID 10641668, compound

HRID 1532730Notes

Reaction equation

HRID 1532730 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][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26]C)=[O:25])=[CH:18][CH:17]=1.[OH-].[Na+]>CO>[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][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10522854HCID 10522854, compound

Product 1

HCID 10641668HCID 10641668, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionate (13.0 g, 35.6 mmol) obtained in Example 16 was dissolved in methanol (400 ml), and 1N aqueous sodium hydroxide solution (50 ml) was added with stirring at room temperature. After stirring for 15 hr, the solvent was evaporated under reduced pressure. Ethyl acetate (50 ml) and water (200 ml) were added for partition. 1N Hydrochloric acid was added to the aqueous layer to acidify same. The precipitated solid was collected by filtration, washed with water (50 ml) and dried under reduced pressure to give the title compound (12.0 g, yield 96%) as a white solid.

Workup

  1. stirringAfter stirring for 15 hr
  2. customthe solvent was evaporated under reduced pressure
  3. additionEthyl acetate (50 ml) and water (200 ml) were added
  4. customfor partition
  5. addition1N Hydrochloric acid was added to the aqueous layer
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with water (50 ml)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-fc414de928f64f858baec441ac68e828
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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