Sulfuric Acid → Methyl 4-oxooxolane-3-carboxylate

HRID 1625993Notes

Reaction equation

HRID 1625993 reaction equation
[H-].[Na+].[C:3]([O:7][CH3:8])(=[O:6])[CH2:4]O.[C:9]([O:13][CH3:14])(=O)[CH:10]=C.S(=O)(=O)(O)[OH:16]>O1CCCC1.CS(C)=O>[O:16]=[C:10]1[CH2:9][O:13][CH2:14][CH:4]1[C:3]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7294Methyl AcrylateHCID 24758Sodium hydrideHCID 66774Methyl Glycolate

Product 1

HCID 14666564Methyl 4-oxooxolane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

55% Sodium hydride (1.9 g) was suspended in tetrahydrofuran (30 ml), and a solution of methyl glycolate (3.6 g) in tetrahydrofuran (10 ml) was added dropwise over 10 minutes. After stirring at room temperature for 30 minutes, the solvent was evaporated to give a colorless solid. This was suspended in dimethyl sulfoxide (20 ml), and methyl acrylate (4.3 ml) was added under ice-cooling. The mixture was stirred at the same temperature for 15 minutes and then stirred at room temperature for 45 minutes. The reaction solution was poured into a 5% aqueous sulfuric acid solution (50 ml), followed by extraction with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (3.0 g) as a colorless solid.

Workup

  1. customthe solvent was evaporated
  2. customto give a colorless solid
  3. temperaturecooling
  4. stirringThe mixture was stirred at the same temperature for 15 minutes
  5. stirringstirred at room temperature for 45 minutes
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated
  10. customThe residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane)

Sources & evidence

ORD record
ord-7d874c8625054dca95a82e9a407760e1
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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