Trifluoroacetic acid → HCID 67485969, compound

HRID 1880585Notes

Reaction equation

HRID 1880585 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1)(O)[CH3:10].[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=1)[CH3:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69311656HCID 69311656, compound

Product 1

HCID 67485969HCID 67485969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
75 °C

Procedure

To the intermediate from Step A (75 mg, 0.23 mmol) in a screw cap tube was added DCM (2 mL), Et3SiH (0.4 mL) and TFA (0.4 mL). The closed tube was then heated at 75° C. for 1.5 hours. The solution was cooled and concentrated. To the residue, which is a mixture of the title compound and methyl 4-[1-(2,5-dichlorophenyl)vinyl]benzoate (1/1), was added DCM (4 mL) and PtO2 (15 mg). The solution was stirred under a hydrogen atmosphere (balloon) for 3 hours. The hydrogen was purged and the solution filtered. The residue was purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound LCMS1 4.19 min. (M+H)=309

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated
  3. additiona mixture of the title compound and methyl 4-[1-(2,5-dichlorophenyl)vinyl]benzoate (1/1)
  4. additionwas added DCM (4 mL) and PtO2 (15 mg)
  5. customThe hydrogen was purged
  6. filtrationthe solution filtered
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-813304fa2013438698fb626fab020252
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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