Sodium Hydroxide → HCID 10763236, compound

HRID 1532723Notes

Reaction equation

HRID 1532723 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:31]=[CH:30][C:19]([CH2:20][CH:21]([C:26]([O:28]C)=[O:27])[C:22]([O:24]C)=[O:23])=[CH:18][CH:17]=1.[OH-].[Na+]>CO.O1CCCC1>[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]([CH2:20][CH:21]([C:26]([OH:28])=[O:27])[C:22]([OH:24])=[O:23])=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 6918417HCID 6918417, compound

Product 1

HCID 10763236HCID 10763236, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]malonate (6.00 g, 14.2 mmol) synthesized according to the method described in WO95/18125 was dissolved in methanol (60 ml) and tetrahydrofuran (30 ml). 2N Aqueous sodium hydroxide solution (17.7 ml, 35.5 mmol) was added at room temperature. The mixture was stirred for 68 hr and the solvent was evaporated. Water (100 ml) was added to the residue and acidified with 1N hydrochloric acid. The precipitated white solid was collected by filtration, washed with water and recrystallized from ethyl acetate-hexane to give the title compound (3.00 g, yield 53%) as a white powder.

Workup

  1. customthe solvent was evaporated
  2. additionWater (100 ml) was added to the residue
  3. filtrationThe precipitated white solid was collected by filtration
  4. washwashed with water
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d9ba4ac6dfac4f84bc4f11d5ebee8efd
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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