4-Phenyl-5-(trifluoromethyl)thiophene-2-carboxylic acid → 1-[4-phenyl-5-(trifluoromethyl)-2-thienyl]ethan-1-one

HRID 552269Notes

Reaction equation

HRID 552269 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]([OH:18])=O)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][CH3:20]>C1COCC1>[C:1]1([C:7]2[CH:8]=[C:9]([C:16](=[O:18])[CH3:20])[S:10][C:11]=2[C:12]([F:13])([F:14])[F:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 27833724-Phenyl-5-(trifluoromethyl)thiophene-2-carboxylic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 27401391-[4-phenyl-5-(trifluoromethyl)-2-thienyl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-phenyl-5-trifluoromethyl-thiophene-2-carboxylic acid (272 mg, 1.0 mmol) in THF (10 mL), a solution of MeLi (1.30 mL, 1.6 M solution in diethyl ether) is added. The dark red reaction mixture is stirred at it for 10 min. The reaction is quenched by adding sat. aq. NH4Cl (10 mL). The organic phase is separated, dried over Na2SO4 and evaporated. The crude product is purified by prep. HPLC (Waters Xterra MS18, 75×30 mm, 10 μm, 10 to 95% acetonitrile in water containing 0.5% formic acid) to give 1-(4-phenyl-5-trifluoromethyl-thiophen-2-yl)-ethanone (31 mg) as pale yellow oil, LC-MS: tR=1.06 min, 1H NMR (CDCl3): δ 7.62-7.60 (m, 1H), 7.45-7.40 (m, 5H), 2.60 (s, 3H).

Workup

  1. customThe dark red reaction mixture
  2. customThe reaction is quenched
  3. additionby adding sat. aq. NH4Cl (10 mL)
  4. customThe organic phase is separated
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-41fde636b53a4103a83c45270e2c376c
Source dataset
uspto-grants-2011_05
Patent number
US07951794B2

Reaction notes

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