Methanol → 2-Thiophenecarboxylic acid, 5-nitro-, methyl ester

HRID 1459438Notes

Reaction equation

HRID 1459438 reaction equation
[N+:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12]O>>[N+:1]([C:4]1[S:8][C:7]([C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 887MethanolHCID 805915-Nitro-2-thenoic acid

Product 1

HCID 799082-Thiophenecarboxylic acid, 5-nitro-, methyl ester

Procedure

To a 500 mL round bottomed flask with a stirring bar, was added 5-nitrothiophene-2-carboxylic acid (4.62 g, 26.68 mmol) and MeOH (100 mL). This solution was cooled in an ice bath and dry HCl gas was bubbled through the solution till saturated. The reaction was equipped with a condensor and a drying tube and refluxed overnight. The solvent was then removed in vacuo to a yellow solid, which was then dissolved in EtOAc. This solution was washed with NaHCO3 (sat, aq) (3×), and brine (2×), dried (MgSO4), and filtered. Removal of the solvents in vacuo and drying of the product in vacuo yielded methyl 5-nitrothiophene-2-carboxylate as a tan solid.

Workup

  1. temperatureThis solution was cooled in an ice bath
  2. customdry HCl gas was bubbled through the solution till saturated
  3. customThe reaction was equipped with a condensor and a drying tube
  4. temperaturerefluxed overnight
  5. customThe solvent was then removed in vacuo to a yellow solid, which
  6. dissolutionwas then dissolved in EtOAc
  7. washThis solution was washed with NaHCO3 (sat, aq) (3×), and brine (2×)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customRemoval of the solvents in vacuo
  11. customdrying of the product in vacuo

Sources & evidence

ORD record
ord-b545dfe2f1214724bfbd17646030ea39
Source dataset
uspto-grants-1998_12
Patent number
US05854245

Reaction notes

Loading…