(E)-5-[4-(Trifluoromethyl)phenyl]-2-penten-4-yn-1-ol → (E)-5-(4-(Trifluoromethyl)phenyl]-2-penten-4-ynal

HRID 1601386Notes

Reaction equation

HRID 1601386 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10]/[CH:11]=[CH:12]/[CH2:13][OH:14])=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[CH:5][C:6]([C:9]#[C:10]/[CH:11]=[CH:12]/[CH:13]=[O:14])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 18363296(E)-5-[4-(Trifluoromethyl)phenyl]-2-penten-4-yn-1-ol

Product 1

HCID 18363293(E)-5-(4-(Trifluoromethyl)phenyl]-2-penten-4-ynalYield 70.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In 4 ml of methylene chloride were dissolved 350 mg (1.56 mmol) of (E)-5-[4-(trifluoromethyl)phenyl]-2-penten-4-yn-1-ol, and 3.5 g of active manganese dioxide were added to the solution, followed by stirring of the resulting mixture at room temperature for 30 minutes. The solid was removed by filtration and the filtrate was concentrated. Then, the filtrate was subjected to column chromatography using 10 g of silica gel and eluted with a mixed solvent of ethyl acetate-hexane (1:24) to obtain 245 mg (yield: 70%) of the title compound as an oil.

Workup

  1. additionwere added to the solution
  2. customThe solid was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. washeluted with a mixed solvent of ethyl acetate-hexane (1:24)

Sources & evidence

ORD record
ord-af8314fb1e5649f48e5a07c08051e656
Source dataset
uspto-grants-1999_11
Patent number
US05977152

Reaction notes

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