Trifluoroacetic acid → Ethyl 5-{3-[(2-oxoethyl)oxy]phenyl}-2-thiophenecarboxylate

HRID 70258Notes

Reaction equation

HRID 70258 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:13]2[S:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>[O:3]=[CH:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([C:13]2[S:17][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58276762HCID 58276762, compound

Product 1

HCID 86641430Ethyl 5-{3-[(2-oxoethyl)oxy]phenyl}-2-thiophenecarboxylate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-(3-{[2,2-bis(ethyloxy)ethyl]oxy}phenyl)-2-thiophenecarboxylate (Intermediate KK-2-3) (1.41 g, 3.87 mmol) was dissolved in 20 ml of chloroform and cooled to 0° C. 5 ml of 50% aqueous trifluoroacetic acid solution was added. The mixture was stirred for 15 h at room temperature and 6 h at 65° C., cooled, diluted with chloroform and neutralized with saturated sodium bicarbonate solution. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (10 to 50% ethyl acetate in hexanes) to afford the title compound as a white crystalline solid.

Workup

  1. temperaturecooled
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (10 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4c98665bd16a49c597e8b882cfa24aab
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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