Dimethyl Sulfate → Dimethyl 3-methoxy-4-methyl-2,5-thiophene dicarboxylate

HRID 1493359Notes

Reaction equation

HRID 1493359 reaction equation
[OH:1][C:2]1[C:3]([CH3:15])=[C:4]([C:11]([O:13][CH3:14])=[O:12])[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[C:16](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:16][O:1][C:2]1[C:3]([CH3:15])=[C:4]([C:11]([O:13][CH3:14])=[O:12])[S:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 54691274Dimethyl 3-hydroxy-4-methyl-2,5-thiophene dicarboxylate

Product 1

HCID 19831300Dimethyl 3-methoxy-4-methyl-2,5-thiophene dicarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of dimethyl 4-hydroxy-3-methyl-2,5-thiophene dicarboxylate (4.26 g) in acetone (100 ml) containing anhydrous potassium carbonate (2.34 g) was stirred for 1 hour at room temperature. Dimethyl sulphate (1.62 ml) was added and the solution refluxed for 2 hours. The solvent was then removed under vacuum and, after treating the residue with water-ethyl acetate, was extracted several times with ethyl acetate; the organic extracts were collected, washed with water, dried over anhydrous magnesium sulphate, filtered and the solvent evaporated to give a solid, m.p. 61°-64° ex methanol.

Workup

  1. temperaturethe solution refluxed for 2 hours
  2. customThe solvent was then removed under vacuum
  3. additionafter treating the residue with water-ethyl acetate
  4. extractionwas extracted several times with ethyl acetate
  5. customthe organic extracts were collected
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. customto give a solid, m.p. 61°-64° ex methanol

Sources & evidence

ORD record
ord-179a3c9e4cec4407a33fae24db07d12a
Source dataset
uspto-grants-1991_06
Patent number
US05021449

Reaction notes

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