Trifluoroacetic acid → HCID 57722978, compound

HRID 1987035Notes

Reaction equation

HRID 1987035 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:12][C:13](C)(C)C)=[O:11])=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH:5]=[C:4]([Cl:24])[N:3]=1.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[CH:5]=[C:4]([Cl:24])[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57722998HCID 57722998, compound

Product 1

HCID 57722978HCID 57722978, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

tert-Butyl 3-[2,6-dichloro-4-(2-chlorophenyl)-3-pyridinyl]propanoate (2.44 g, 6.31 mmol) was dissolved in anisole (6 ml) and trifluoroacetic acid (30 ml) added and the solution allowed to stand at 21° for 2 h, then evaporated in vacuo. The residue was dissolved in toluene (40 ml)-methanol (10 ml), and a 2M solution of trimethylsilyldiazomethane in hexanes added (8 ml), and the solution allowed to stand for 0.5 h. The solution was evaporated in vacuo, and the resulting oil purified by flash chromatography over silica eluting with cyclohexane-ethyl acetate (100:0-65:35) to give the title compound as a viscous gum (1.40 g, 64%)

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in toluene (40 ml)-methanol (10 ml)
  3. additiona 2M solution of trimethylsilyldiazomethane in hexanes added (8 ml)
  4. waitto stand for 0.5 h
  5. customThe solution was evaporated in vacuo
  6. customthe resulting oil purified by flash chromatography over silica eluting with cyclohexane-ethyl acetate (100:0-65:35)

Sources & evidence

ORD record
ord-3711ce8d3fa94adf8430d58378de2b62
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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