2-Oxime 2,3-butanedione → HCID 86605723, compound

HRID 2221590Notes

Reaction equation

HRID 2221590 reaction equation
C([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1)=O.[CH3:15][C:16](=[N:20]O)C(=O)C.[ClH:22].[C:23]([O:26][CH2:27][CH3:28])(=O)C>C(OCC)C>[Cl:22][CH2:15][C:16]1[N:20]=[C:23]([C:8]2[CH:3]=[CH:4][C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=2)[O:26][C:27]=1[CH3:28]

Participants

5

Reactant 3

HCID 63989692-Oxime 2,3-butanedioneHCID 21866389Hydrogen chloride-ethyl acetateHCID 23076590Ethyl 2-(3-formylphenyl)acetate

Product 1

HCID 86605723HCID 86605723, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethyl 3-formylphenylacetate (1.52 g), 2,3-butanedione-2-oxime (0.80 g) and 4N hydrogenchloride-ethyl acetate solution (30 mL) was stirred at room temperature for 2 days. After concentration of the reaction mixture, diethyl ether was added to the residue and the precipitated crystals were collected by filtration. A mixture of the obtained crystal, tetrahydrofuran (50 mL) and thionyl chloride (1.42 g) was heated under reflux for 1 hr. After concentration of the reaction mixture, saturated aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give ethyl [4-(4-chloromethyl-5-methyl-1,3-oxazol-2-yl)phenyl]acetate as colorless crystals (0.85 g, yield 37%) from a fraction eluted with ethyl acetate-hexane (1:6, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 87-88° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. additionA mixture of the obtained crystal, tetrahydrofuran (50 mL) and thionyl chloride (1.42 g)
  3. temperaturewas heated
  4. temperatureunder reflux for 1 hr
  5. additionAfter concentration of the reaction mixture, saturated aqueous sodium hydrogen carbonate was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe ethyl acetate layer was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f35397405b194490b61eeb099323e2d5
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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