Methanol → 2,5-Dimethyl-3-thiopheneacetic acid

HRID 229748Notes

Reaction equation

HRID 229748 reaction equation
[OH-:1].[Na+].[CH3:3][C:4]1[S:5][C:6]([CH3:18])=[CH:7][C:8]=1[CH2:9][C:10](N1CCOCC1)=S.C[OH:20]>>[CH3:3][C:4]1[S:5][C:6]([CH3:18])=[CH:7][C:8]=1[CH2:9][C:10]([OH:20])=[O:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 142499202-(2,5-Dimethyl-3-thienyl)-1-(4-morpholinyl)ethanethione

Product 1

HCID 142499212,5-Dimethyl-3-thiopheneacetic acid

Procedure

2-(2,5-Dimethyl-3-thienyl)acetic acid is prepared according to a method described in Heterocycl. Chem; EN; 25; 1988; 1571-1581. 21 ml of an aqueous sodium hydroxide solution (50% by mass) are added to 6.7 g of 2-(2,5-dimethyl-3-thienyl)-1-(4-morpholinyl)-1-ethanethione obtained in step 2.1, in solution in 70 ml of methanol, and the mixture is heated for 6 hours under reflux. After evaporation of the methanol, the residue is diluted with water and acidified with an aqueous hydrochloric acid solution (6N). The precipitate formed is filtered and then it is chromatographed on a silica gel column, eluting with dichloromethane to give 3.6 g of beige crystals.

Workup

  1. temperaturethe mixture is heated for 6 hours
  2. temperatureunder reflux
  3. customAfter evaporation of the methanol
  4. additionthe residue is diluted with water
  5. customThe precipitate formed
  6. filtrationis filtered
  7. customit is chromatographed on a silica gel column
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-35fb974bae43435692e9129153335508
Source dataset
uspto-grants-2009_07
Patent number
US07563903B2

Reaction notes

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