Methyl iodide → Methyl 5-acetylthiophene-2-carboxylate

HRID 660968Notes

Reaction equation

HRID 660968 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:12](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:12][O:10][C:9]([C:7]1[S:8][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1)=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 37427275-Acetylthiophene-2-carboxylic acid

Product 1

HCID 13156400Methyl 5-acetylthiophene-2-carboxylateYield 60.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-acetyl-thiophene-2-carboxylic acid (1 g, 5.88 mmol) in DMF (24 mL) is treated with potassium carbonate (813 mg, 5.88 mmol), then iodomethane (0.368 mL, 5.88 mmol), and stirred for 60 h at rt. The reaction mixture is acidified and extracted into ethyl acetate twice. The combined organic layers are washed with brine, dried, filtered, and concentrated, then taken up in ethyl acetate, washed with saturated aqueous potassium carbonate, dried, filtered and concentrated to give 5-acetyl-thiophene-2-carboxylic acid methyl ester (653 mg).

Workup

  1. extractionextracted into ethyl acetate twice
  2. washThe combined organic layers are washed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washwashed with saturated aqueous potassium carbonate
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4d4c9394cd36476db734bf55b32ccb1c
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

Loading…