Lithium Hydroxide → 5-(2,2,2-Trifluoroacetyl)thiophene-2-carboxylic acid

HRID 1715344Notes

Reaction equation

HRID 1715344 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[S:9][C:8]([C:10]([O:12]CC)=[O:11])=[CH:7][CH:6]=1)=[O:4].[Li+].[OH-]>CO.O>[F:16][C:2]([F:1])([F:15])[C:3]([C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 24726843Ethyl 5-trifluoroacetyl-2-thenoate

Product 1

HCID 242747015-(2,2,2-Trifluoroacetyl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Ethyl 5-(trifluoroacetyl)thiophene-2-carboxylate was hydrolysed with LiOH (2.1 eq.) in MeOH/H2O (1:1) at RT for 48 h. The mixture was concentrated under reduced pressure and extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated under reduced pressure to give the title compound as white solid. MS (ES) C7H3F3O3S requires: 224, found: 243 (M+H2O+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e63f3e69eab4a4a8d4bcded5c82f4a6
Source dataset
uspto-grants-2010_09
Patent number
US07799825B2

Reaction notes

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