Acetic Acid → Methyl 2-{(benzofuran-5-yl)methylene}-3-oxobutyrate

HRID 2085380Notes

Reaction equation

HRID 2085380 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:11]=1)=NON=2)=O.[C:12]([O:18][CH3:19])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CCCCC1.[C:26]([OH:29])(=O)[CH3:27]>C1C=CC=CC=1>[O:29]1[C:26]2[CH:27]=[CH:1][C:3]([CH:11]=[C:13]([C:14](=[O:15])[CH3:16])[C:12]([O:18][CH3:19])=[O:17])=[CH:4][C:5]=2[CH:6]=[CH:7]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7757Methyl acetoacetateHCID 8082PiperidineHCID 2776296Benzo(c)(1,2,5)oxadiazole-5-carbaldehyde

Product 1

HCID 54375059Methyl 2-{(benzofuran-5-yl)methylene}-3-oxobutyrate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5-formylbenzofurazan (0.60 g, 4.1 mmol), methyl acetoacetate (0.52 g, 4.5 mmol), piperidine (0.019 g, 0.23 mmol), and acetic acid (0.014 g, 0.23 mmol) in benzene (30 mL) was heated at reflux temperature (equipped with a Dean-Stark trap) for 8 h. Benzene was evaporated in vacuo, the residue was dissolved in ethyl acetate (80 mL) and washed with brine (50 mL), saturated potassium bisulfate solution (50 mL), and saturated sodium bicarbonate solution. The ethyl acetate solution was dried over magnesium sulfate, the solvent removed under reduced pressure and the residue was purified by column chromatography (EtOAc/hexane, 1/9 to 3/20). The desired product was obtained as oil (0.98 g, 98%) and was used in the next step without any further characterization.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature (
  3. customequipped with a Dean-Stark trap) for 8 h
  4. customBenzene was evaporated in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate (80 mL)
  6. washwashed with brine (50 mL), saturated potassium bisulfate solution (50 mL), and saturated sodium bicarbonate solution
  7. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  8. customthe solvent removed under reduced pressure
  9. customthe residue was purified by column chromatography (EtOAc/hexane, 1/9 to 3/20)

Sources & evidence

ORD record
ord-0b356dcec6c2430890841d209ca78ab6
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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