Methanol → Methyl alpha-oxo-2-thiopheneacetate

HRID 1080709Notes

Reaction equation

HRID 1080709 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[C:7]([OH:9])=[O:8].[CH3:11]O>CCC(CCCCC(NC(C(NC(C(NC(C(NC1C(=O)NC(CCN)C(=O)NC(CC2C=CC=CC=2)C(=O)NC(CC(C)C)C(=O)NC(CCN)C(=O)NC(CCN)C(=O)NC(C(O)C)C(=O)NCC1)=O)CCN)=O)C(O)C)=O)CCN)=O)C.OS(O)(=O)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[C:7]([O:9][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 887MethanolHCID 776942-Thiopheneglyoxylic acid

Product 1

HCID 11217486Methyl alpha-oxo-2-thiopheneacetate

Reagents, catalysts & solvents 1

HCID 5702105AerosporinCatalyst

Procedure

To a stirred solution of 2-thiopheneglyoxylic acid (1 g) in methanol (10 ml) was added 5 drops of concentrated sufuric acid and the mixture was refluxed for 4 hours. Then the methanol was evaporated off and the residue was partitioned between ethyl acetate and water. The organic extract was washed with water and brine, dried (sodium sulfate) and evaporated to give methyl 2-thiopheneglyoxylate as an oil (1.01 g).

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customThen the methanol was evaporated off
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried (sodium sulfate)
  7. customevaporated

Sources & evidence

ORD record
ord-47a308e96fc2458889aa3190145ccd5c
Source dataset
uspto-grants-1996_12
Patent number
US05583147

Reaction notes

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