Trifluoroacetic acid → 31040-76-3

HRID 854889Notes

Reaction equation

HRID 854889 reaction equation
[OH:1][C:2]1[C:3]([CH3:16])=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.[NH4+].[Cl-]>C(Cl)Cl>[CH2:8]([C:4]1[C:3]([CH3:16])=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 25517Ammonium ChlorideHCID 12639787HCID 12639787, compound

Product 1

HCID 5343099531040-76-3Yield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (3-hydroxy-2-methylphenyl)(phenyl)methanone prepared as in Step 2 (1.60 g, 7.54 mmole) in anhydrous CH2Cl2 (70 mL) was cooled to 0° C. Triethylsilane (32.5 mL, 203 mmole) and TFA (52.3 mL, 679 mmole) were added in portions at 0° C. over a period of 3 days with the mixture brought back to reflux after each addition. After 3 days, the mixture was cooled, poured into sat. NH4Cl (200 mL) and extracted with CH2Cl2 (3×200 mL). The combined extracts were washed with H2O (200 mL), brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The crude product was purified by silica chromatography (95:5 hexanes:EtOAc) to give 1.19 g (80% yield) of the product as a pale yellow oil: EIHRMS m/z 198.1072 (M+, C14H14O, Calc'd 198.1045).

Workup

  1. temperatureto reflux
  2. additionafter each addition
  3. temperaturethe mixture was cooled
  4. extractionextracted with CH2Cl2 (3×200 mL)
  5. washThe combined extracts were washed with H2O (200 mL), brine (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a yellow oil
  10. customThe crude product was purified by silica chromatography (95:5 hexanes:EtOAc)

Sources & evidence

ORD record
ord-b567b7eee32849348bab8871199474d9
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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