Methanol → Methyl 5-methyl-4-nitrothiophene-2-carboxylate

HRID 505775Notes

Reaction equation

HRID 505775 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].S(=O)(=O)(O)O.O.[CH3:19]O>CCOC(C)=O>[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:19])=[O:8])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 31107845-Methyl-4-nitrothiophene-2-carboxylic acid

Product 1

HCID 268679Methyl 5-methyl-4-nitrothiophene-2-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution (0.5 M) of 5-methyl-4-nitrothiophene-2-carboxylic acid in methanol was treated with sulfuric acid (3.5 eq.). The reaction mixture was heated to reflux for 48 h. After cooling down, solvent was evaporated giving a residue that was dissolved in AcOEt and water was added. The organic phase was separated and the aqueous layer was extracted with AcOEt. The combined organic phase was washed sequentially with aqueous NaHCO3 (saturated solution) and brine, then dried and concentrated giving the title compound (69%) as solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 48 h
  3. temperatureAfter cooling down
  4. customsolvent was evaporated
  5. customgiving a residue that
  6. customThe organic phase was separated
  7. extractionthe aqueous layer was extracted with AcOEt
  8. washThe combined organic phase was washed sequentially with aqueous NaHCO3 (saturated solution) and brine
  9. customdried
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e6e58a96d6c048e3ae14085febf681a5
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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