Methyl iodide → 5-(Methoxycarbonyl)thiophene-2-carboxylic acid

HRID 555611

Reaction equation

HRID 555611 reaction equation
[S:1]1[C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=[C:2]1[C:9]([OH:11])=[O:10].[C:12](=O)([O-])[O-].[Na+].[Na+].CI>CN(C=O)C>[CH3:12][O:7][C:6]([C:5]1[S:1][C:2]([C:9]([OH:11])=[O:10])=[CH:3][CH:4]=1)=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 202732,5-Thiophenedicarboxylic acid

Product 1

HCID 8183525-(Methoxycarbonyl)thiophene-2-carboxylic acidYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.72 g (10 mmol) of thiophene-2,5-dicarboxylic acid and 3.18 g (30 mmol) of sodium carbonate suspended in 25 mL of DMF were stirred with 623 μL of methyl iodide at room temperature overnight. The sodium salt of the desired product was extracted with water, and 12M of hydrochloric acid was added to the combined aqueous layer. The desired product was extracted with ethyl acetate, and the combined organic layer was washed with saturated aqueous ammonium chloride and dried over anhydrous magnesium sulfate. The desired product was purified by silica gel column chromatography to give 0.49 g of a colorless solid (yield 28%).

Workup

  1. extractionThe sodium salt of the desired product was extracted with water, and 12M of hydrochloric acid
  2. additionwas added to the combined aqueous layer
  3. extractionThe desired product was extracted with ethyl acetate
  4. washthe combined organic layer was washed with saturated aqueous ammonium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe desired product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-20ff9d668ba74d5ba34d3fbdb9664090
Source dataset
uspto-grants-2011_11
Patent number
US08053453B2

Linked notes

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