Methanol → 6-(Trifluoromethyl)benzo[b]thiophene-2-carboxylic acid
Reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:6]2[CH:7]=[C:8]([C:10]([O:12]CC)=[O:11])[S:9][C:5]=2[CH:4]=1.CO.[Li+].[OH-].O>C1COCC1>[F:17][C:2]([F:1])([F:18])[C:3]1[CH:16]=[CH:15][C:6]2[CH:7]=[C:8]([C:10]([OH:12])=[O:11])[S:9][C:5]=2[CH:4]=1Participants
Procedure
To ethyl 6-(trifluoromethyl)-1-benzothiophene-2-carboxylate dissolved in THF and MeOH was added a solution of LiOH in H2O (1.5 equiv). The reaction media became cloudy so H2O, MeOH and THF were added until a clear solution ensued (Final composition of media=2 THF:1 MeOH:1 H2O) (0.2 M). After 1 h, analysis showed consumption of all the starting material. A large proportion of the volatiles were removed under reduced pressure. The remaining solution was treated with 1N HCl. The precipitate was filtered off and dissolved in a mixture of THF, MeOH and EtOAc. The organic solution was dried over magnesium sulfate and concentrated under reduced pressure to obtain the title compound as a solid. The latter was ground with a mortar and pestle and let dry overnight under high vacuum.
Workup
- customThe reaction media
- additionwere added until a clear solution
- customconsumption of all the starting material
- customA large proportion of the volatiles were removed under reduced pressure
- additionThe remaining solution was treated with 1N HCl
- filtrationThe precipitate was filtered off
- dissolutiondissolved in a mixture of THF, MeOH and EtOAc
- dry with materialThe organic solution was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-30e7e469bb44412cb3da4dba89fc081e
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08518964B2
Reaction notes
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