HCID 18000976, compound → HCID 18000977, compound

HRID 478291Notes

Reaction equation

HRID 478291 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[C:8]([F:9])([F:10])[F:11])[CH:12]=[O:13]

Participants

4

Reactant 1

HCID 18000976HCID 18000976, compound

Product 1

HCID 18000977HCID 18000977, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

The product from Example 62C in chloroform (60 mL) was treated with manganese dioxide (1.45 g, 16 mmol). After refluxing for 12 hours, the mixture was allowed to cool to ambient temperature, filtered and the filtrate concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 15% ethyl acetate:hexanes to provide the title compound (0.5 g, 42% yield).

Workup

  1. temperatureAfter refluxing for 12 hours
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customThe residue was chromatographed on silica gel eluting with 15% ethyl acetate

Sources & evidence

ORD record
ord-20ec256d8fcb4ac3b13a67e0451e102b
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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