Sodium Chloride → Methyl 4-acetylthiophene-2-carboxylate

HRID 1463485Notes

Reaction equation

HRID 1463485 reaction equation
CI.[C:3]([C:6]1[CH:7]=[C:8]([C:11]([OH:13])=[O:12])[S:9][CH:10]=1)(=[O:5])[CH3:4].[C:14](=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>CN(C)C=O.O>[C:3]([C:6]1[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[S:9][CH:10]=1)(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 131564014-Acetylthiophene-2-carboxylic acid

Product 1

HCID 13156397Methyl 4-acetylthiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyliodide (783 mg, 5.51 mmoles) was added to a stirred suspension of 4-acetyl-2-thiophenecarboxylic acid (prepared according to Satonaka, H., Bull. Chem. Soc. Japan 56:2463 (1983)) (782 mg, 4.59 mmoles) and sodium carbonate (1.70 g, 16.08 mmoles) in 25 ml of N,N-dimethylformamide. After stirring overnight at room temperature the mixture was poured into water (125 ml), saturated with solid sodium chloride and extracted with ethyl acetate (3×50 ml). The combined extracts were washed with brine, dried (magnesium sulfate) and concentrated in vacuo to an off-white solid (761 mg, 90%), m.p. 94°-6° C. EIMS (m/z): 184 (M+, 74%), 169 (M+ --CH base), 153 (M+ --CH3O, 51%); 1HNMR (DMSO-d6) delta, 8.17 (1H, d, J=1.5 Hz), 8.13 (1H, d, J=1.5 Hz), 3.88 (3H, s), 2.51 (3H, s).

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated in vacuo to an off-white solid (761 mg, 90%), m.p. 94°-6° C

Sources & evidence

ORD record
ord-7960bcc6dbc846219b6fcff002ec2793
Source dataset
uspto-grants-1994_04
Patent number
US05300655

Reaction notes

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