Sodium Hydroxide → HCID 22613014, compound

HRID 844363Notes

Reaction equation

HRID 844363 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[C:12]([C:14](=[O:22])[CH2:15][C:16](=[O:21])[C:17]([O:19]C)=[O:18])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.C(Cl)(Cl)Cl>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[C:12]([C:14](=[O:22])[CH2:15][C:16](=[O:21])[C:17]([OH:19])=[O:18])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22613011HCID 22613011, compound

Product 1

HCID 22613014HCID 22613014, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[5-benzyl-2-(pyridin-2-yloxy)phenyl]-2,4-dioxo-butyrate (0.14 g) in THF (10 mL) at room temp., aq. NaOH (1 M, 0.44 mL) was added. The resultant mixture was stirred at room temp for 6 h. The product mixture was diluted with chloroform and partitioned with aq. HCl. The organic extract was washed with brine, dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was triturated with a mixture of diethyl ether and hexane. Filtration of the resultant solid provided the title acid. 1H NMR (CDCl3) δ8.25 (m, 1H), 7.8-6.8 (m, 12H), 4.05 (s, 2H).

Workup

  1. custompartitioned with aq. HCl
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was triturated with a mixture of diethyl ether and hexane
  8. filtrationFiltration of the resultant solid
  9. customprovided the title acid

Sources & evidence

ORD record
ord-07ee17cc34fb4145b9129b28a05a9292
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

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