HCID 18000976, compound → HCID 18000977, compound

HRID 987384Notes

Reaction equation

HRID 987384 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 4C 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-c0e4f3a03099414e989e990f661d2869
Source dataset
uspto-grants-2003_10
Patent number
US06632418B2

Reaction notes

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