Sulfuric Acid → Methyl 4-oxooxolane-3-carboxylate

HRID 2251130Notes

Reaction equation

HRID 2251130 reaction equation
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=O)[CH2:4][OH:5].[C:10]([O:14][CH3:15])(=[O:13])C=C.OS(O)(=O)=O>CCOCC.CS(C)=O>[CH3:15][O:14][C:10]([CH:9]1[C:4](=[O:5])[CH2:3][O:7][CH2:8]1)=[O:13]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7294Methyl AcrylateHCID 12184Ethyl GlycolateHCID 24758Sodium hydride

Product 1

HCID 14666564Methyl 4-oxooxolane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred slurry of sodium hydride (1.67 g, 60% in mineral oil, 44.0 mmol) in dried ether was added with ethyl glycolate, dropwise over 15 minutes. The reaction was warmed up to room temperature for 30 min while stirring and concentrated in vacuo to provide white solid. The solid was treated with methyl acrylate (4.16 g, 49 mmol) in DMSO (20 mL) at 0° C. for 15 minutes and room temperature for 45 minutes. The mixture was poured into 5% H2SO4 and extracted with ethyl acetate. Organic layer was washed with brine, dried over Mg2SO4 and concentrated to give 4-oxo-tetrahydro-furan-3-carboxylic acid methyl ester as a colorless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customto provide white solid
  3. extractionextracted with ethyl acetate
  4. washOrganic layer was washed with brine
  5. dry with materialdried over Mg2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-16f1e0359077471fa02bcd2e945e18fc
Source dataset
uspto-grants-2008_01
Patent number
US07319103B2

Reaction notes

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