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

HRID 1881536Notes

Reaction equation

HRID 1881536 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)C=O>[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

Thiophene-2,5-dicarboxylic acid (1.72 g, 10 mmol) and sodium carbonate (3.18 g, 30 mmol) suspended in dimethylformamide (25 mL) were stirred with methyl iodide (623 μL) at room temperature overnight. The sodium salt of the desired product was extracted with water, and 12 M 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, dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to give 0.49 g of the desired product as a colorless solid (yield 28%).

Workup

  1. extractionThe sodium salt of the desired product was extracted with water, and 12 M 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. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-459b338540b44ab8bb35e3a539af70e4
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

Loading…