HCID 22613055, compound → HCID 22613202, compound

HRID 844364Notes

Reaction equation

HRID 844364 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([O:26][CH3:27])[C:11]([O:24][CH3:25])=[C:12]([C:14](=[O:23])[CH2:15][C:16](=[O:22])[C:17]([O:19]CC)=[O:18])[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[OH-].[Na+]>[CH2:1]([C:8]1[CH:9]=[C:10]([O:26][CH3:27])[C:11]([O:24][CH3:25])=[C:12]([C:14](=[O:23])[CH2:15][C:16](=[O:22])[C:17]([OH:19])=[O:18])[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 22613055HCID 22613055, compound

Product 1

HCID 22613202HCID 22613202, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of ethyl 4-(5-benzyl-2,3-dimethoxyphenyl)-2,4-dioxobutyrate (0.59 g) in ethanol (8 mL), aq. NaOH (1 M, 6.4 mL) was added. The resultant mixture was stirred at room temp for 2 h. The product mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate and aq. HCl. The organic extract was washed with brine, dried over magnesium 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) δ7.4-7.2 (m, 7H), 6.92 (br s, 1H), 3.97 (s, 2H), 3.89 (s, 3H), 3.84 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-5d9371eed52941d7ba7960df814ed4b1
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

Loading…