Trifluoroacetic acid → HCID 57424264, compound

HRID 2377481Notes

Reaction equation

HRID 2377481 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[Br:17])=O)[CH3:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][CH2:7][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[Br:17])[CH3:2]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 57424263HCID 57424263, compound2×

Product 1

HCID 57424264HCID 57424264, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 4-(2-bromo-4-methoxy-phenyl)-4-oxo-butyric acid ethyl ester (Intermediate 150, 6.45 g, 20.5 mmol) in trifluoroacetic acid (32 mL, 409 mmol) was treated with triethylsilane (14.4 mL, 90 mmol) and the resulting reaction mixture was heated at 55° C. for 3 h. The reaction mixture was then cooled to ambient temperature, neutralized with solid sodium bicarbonate, diluted with water and extracted with diethyl ether. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound (5.4 g, 88%) as a colorless oil.

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was then cooled to ambient temperature
  3. extractionextracted with diethyl ether
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-cc18466c943c4a9eba7c8936effdfbfb
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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