Phosphorus oxychloride → 2-Methylthiophene-3-carboxylic acid

HRID 1814505Notes

Reaction equation

HRID 1814505 reaction equation
COC1C=CC(C2N[C:13](=[O:15])[C:12]3[CH:16]=[CH:17][S:18][C:11]=3[CH:10]=2)=CC=1.P(Cl)(Cl)(Cl)=[O:20]>>[CH3:10][C:11]1[S:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:20]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 225033756(4-Methoxyphenyl)-5h-thieno[3,2-c]pyridin-4-one

Product 1

HCID 46254092-Methylthiophene-3-carboxylic acidYield 131.3%

Conditions

Temperature
120 °C

Procedure

6-(4-Methoxyphenyl)-5H-thieno[3,2-c]pyridin-4-one (9.1 g) was added to phosphorus oxychloride (90 g), and the mixture was heated at 120° C. for 3 hr. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and water. The organic layer was washed with water, an aqueous solution of saturated sodium bicarbonate and brine, and dried over magnesium sulfate. The solvent was evaporate, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a white powder (6.6 g, yield; 73%).

Workup

  1. customThe reaction solution was evaporated
  2. additionto the resulting residue were added ethyl acetate and water
  3. washThe organic layer was washed with water
  4. dry with materialan aqueous solution of saturated sodium bicarbonate and brine, and dried over magnesium sulfate
  5. customThe solvent was evaporate
  6. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-71fec2da89c24236aa884e0e05fd0281
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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