Sodium Hydroxide → HCID 9866203, compound

HRID 1532720Notes

Reaction equation

HRID 1532720 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][CH3:25])=[O:23])=[CH:18][CH:17]=1.[OH-].[Na+]>CO.O1CCCC1>[CH3:25][O:24][C:22]([CH:21]([CH2:20][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:31][CH:30]=1)[C:26]([OH:28])=[O:27])=[O:23]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 6918417HCID 6918417, compound

Product 1

HCID 9866203HCID 9866203, compoundYield 6.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]malonate (8.46 g, 20 mmol) synthesized according to the method described in WO95/18125 was dissolved in a mixture of methanol (80 ml) and tetrahydrofuran (40 ml), and 2N aqueous sodium hydroxide solution (11 ml, 22 mmol) was added at 0° C. The mixture was stirred for 1.5 hr at room temperature and the solvent was evaporated. A saturated aqueous solution (5 ml) of sodium hydrogencarbonate was added and the aqueous layer was washed with ethyl acetate. To the obtained aqueous layer was added sodium chloride to saturate the solution, and the mixture was acidified with 1N hydrochloric acid and washed three times with ethyl acetate (50 ml). The extracted organic layers were combined, washed with brine, dried over sodium sulfate and dried to solidness to give a crude title compound (8.2 g, yield 100%). The obtained crude compound (750 mg) was recrystallized from a mixed solvent of ethyl acetate-hexane (1:2) to give the title compound (540 mg) as a white solid.

Workup

  1. additionwas added at 0° C
  2. customthe solvent was evaporated
  3. additionA saturated aqueous solution (5 ml) of sodium hydrogencarbonate was added
  4. washthe aqueous layer was washed with ethyl acetate
  5. additionTo the obtained aqueous layer was added sodium chloride
  6. concentrationto saturate the solution
  7. washwashed three times with ethyl acetate (50 ml)
  8. washwashed with brine
  9. dry with materialdried over sodium sulfate
  10. customdried to solidness
  11. customto give a crude title compound (8.2 g, yield 100%)
  12. customThe obtained crude compound (750 mg)
  13. customwas recrystallized from a mixed solvent of ethyl acetate-hexane (1:2)

Sources & evidence

ORD record
ord-04870b2766ed47e8ab3ce8bf3699b896
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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