Methanol → 2,5-Dimethyl-3-thiopheneacetic acid
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
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
- temperaturethe mixture is heated for 6 hours
- temperatureunder reflux
- customAfter evaporation of the methanol
- additionthe residue is diluted with water
- customThe precipitate formed
- filtrationis filtered
- customit is chromatographed on a silica gel column
- washeluting with dichloromethane
Sources & evidence
- ORD record
- ord-021e7f31f34e4ce1a89a9b3702f322aa
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879889B2
Reaction notes
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