2-Oxime 2,3-butanedione → HCID 86605726, compound

HRID 2221592Notes

Reaction equation

HRID 2221592 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5](CC(OC)=O)[CH:6]=[CH:7][CH:8]=1)=O.[CH3:14][C:15](=[N:19]O)[C:16](=[O:18])[CH3:17].[ClH:21].[C:22]([O:25][CH2:26][CH3:27])(=[O:24])[CH3:23]>C(OCC)C>[Cl:21][CH2:14][C:15]1[N:19]=[C:1]([C:3]2[CH:4]=[C:5]([CH2:23][C:22]([O:25][CH2:26][CH3:27])=[O:24])[CH:6]=[CH:7][CH:8]=2)[O:18][C:16]=1[CH3:17]

Participants

5

Reactant 3

HCID 63989692-Oxime 2,3-butanedioneHCID 11819590Methyl 2-(3-formylphenyl)acetateHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 86605726HCID 86605726, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 3-formylphenylacetate (16.20 g), 2,3-butanedione-2-oxime (8.52 g) and 4N hydrogenchloride-ethyl acetate solution (300 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 (300 mL) and thionyl chloride (14.99 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 [3-(4-chloromethyl-5-methyl-1,3-oxazol-2-yl)phenyl]acetate as colorless crystals (11.77 g, yield 48%) from a fraction eluted with ethyl acetate-hexane (1:6, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 64-65° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. additionA mixture of the obtained crystal, tetrahydrofuran (300 mL) and thionyl chloride (14.99 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-0636dfd801e44f85a0bc1bd01c2d1bb3
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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