Water → Methyl 3-acetylthiophene-2-carboxylate

HRID 357756Notes

Reaction equation

HRID 357756 reaction equation
[C:1]([C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]([OH:11])=[O:10])(=[O:3])[CH3:2].IC.[C:14](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:14][O:10][C:9]([C:5]1[S:6][CH:7]=[CH:8][C:4]=1[C:1](=[O:3])[CH3:2])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 8189273-acetylthiophene-2-carboxylic acid

Product 1

HCID 13156393Methyl 3-acetylthiophene-2-carboxylateYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Acetyl-2-thiophenecarboxylic acid (3.0 g) was dissolved in N,N-dimethylformamide (50 ml), and iodomethane (4.0 ml) and potassium carbonate (6.0 g) were added. The mixture was stirred at room temperature for 3 hours, poured into water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 3-acetyl-2-thiophenecarboxylic acid methyl ester (3.07 g) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-398ade673da34c7fb5ce5c4962a77173
Source dataset
uspto-grants-1998_11
Patent number
US05840917

Reaction notes

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