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

HRID 379956Notes

Reaction equation

HRID 379956 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-9920da54fb77480c9c10d9e1b93d7a8c
Source dataset
uspto-grants-2001_10
Patent number
US06300357B1

Reaction notes

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