Methanol → methyl 2-oxo-4-phenylbut-3-enoate

HRID 887890Notes

Reaction equation

HRID 887890 reaction equation
S(=O)(=O)(O)O.[O:6]=[C:7]([CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([O-:10])=[O:9].[Na+].[CH3:20]O>>[O:6]=[C:7]([CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([O:10][CH3:20])=[O:9]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 68494475HCID 68494475, compound

Product 1

HCID 582963methyl 2-oxo-4-phenylbut-3-enoate

Procedure

2 ml of concentrated sulfuric acid are added dropwise to a suspension of 5.9 g (30 mmol) sodium 2-oxo-4-phenylbut-3-enoate (1) (Synth. Commun., (1996), 26(11), 2231) in 100 ml of methanol. The mixture is refluxed for 8 hours and stirred overnight at room temperature. A light insoluble material is filtered off and the filtrate is concentrated to half its volume and poured into 300 ml of water. The pasty solid obtained is extracted with dichloromethane and washed with aqueous 5% sodium hydrogen carbonate solution and then with water. The resulting solution is dried over sodium sulfate. The solvent is evaporated off under vacuum. The residue (4.2 g) is purified by flash chromatography (SiO2, 70/30 CH2Cl2/heptane).

Workup

  1. temperatureThe mixture is refluxed for 8 hours
  2. filtrationA light insoluble material is filtered off
  3. concentrationthe filtrate is concentrated to half its volume
  4. additionpoured into 300 ml of water
  5. customThe pasty solid obtained
  6. extractionis extracted with dichloromethane
  7. washwashed with aqueous 5% sodium hydrogen carbonate solution
  8. dry with materialThe resulting solution is dried over sodium sulfate
  9. customThe solvent is evaporated off under vacuum
  10. customThe residue (4.2 g) is purified by flash chromatography (SiO2, 70/30 CH2Cl2/heptane)

Sources & evidence

ORD record
ord-9d377630f6eb4d1e80f400af68caddee
Source dataset
uspto-grants-2012_08
Patent number
US08247448B2

Reaction notes

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