Ethyl 4-phenyl-5-(trifluoromethyl)thiophene-2-carboxylate → 4-Phenyl-5-(trifluoromethyl)thiophene-2-carboxylic acid

HRID 552268Notes

Reaction equation

HRID 552268 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([C:17]([F:20])([F:19])[F:18])=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:10]=1)=[O:5])C>C(O)C.[Li+].[OH-].O>[C:11]1([C:9]2[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[S:7][C:8]=2[C:17]([F:19])([F:20])[F:18])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 1

HCID 2781475Ethyl 4-phenyl-5-(trifluoromethyl)thiophene-2-carboxylate

Product 1

HCID 27833724-Phenyl-5-(trifluoromethyl)thiophene-2-carboxylic acidYield 98.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3939Lithium HydroxideSolvent

Procedure

A solution of 4-phenyl-5-trifluoromethyl-thiophene-2-carboxylic acid ethyl ester (750 mg, 2.50 mmol) in ethanol (12 mL) and 2 N aq. LiOH (6 mL) is stirred at 65° C. for 2 h. The reaction mixture is cooled to rt, diluted with water (60 mL) and extracted with DCM (50 mL). The aq. phase is acidified by adding 2 N aq. HCl (7 mL) and extracted twice with DCM (2×50 mL). These organic extracts are combined, washed with sat. aq. NaHCO3, dried over Na2SO4, evaporated and dried under high vacuum to give 4-phenyl-5-trifluoromethyl-thiophene-2-carboxylic acid (670 mg) as a brown solid, LC-MS: tR=0.97 min, 1H NMR (D6-DMSO): δ 7.57-7.54 (m, 1H), 7.46-7.42 (m, 5H).

Workup

  1. extractionextracted with DCM (50 mL)
  2. additionby adding 2 N aq. HCl (7 mL)
  3. extractionextracted twice with DCM (2×50 mL)
  4. washwashed with sat. aq. NaHCO3
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-551cfc77f3f44fbaa75ec97cf1d0ab88
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

Loading…