HCID 66705812, compound → HCID 86637810, compound

HRID 425425Notes

Reaction equation

HRID 425425 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][C:9]=2[CH2:13][OH:14])=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH2:11][CH2:10][C:9]=2[CH:13]=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66705812HCID 66705812, compound

Product 1

HCID 86637810HCID 86637810, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Manganese (IV) oxide (activated, Aldrich) (4.04 g, 46.5 mmol) was added to a solution of [2-(4-bromophenyl)cyclopent-1-en-1-yl]methanol (3.36 g, 13.3 mmol) in chloroform (25 mL) at ambient temperature. After stirring at reflux overnight, the reaction was filtered through celite (rinsing with methylene chloride) and concentrated. Chromatography over silica eluting with 0-20% ethyl acetate/hexane afforded 2-(4-bromophenyl)cyclopent-1-ene-1-carbaldehyde as an off-white solid.

Workup

  1. temperatureat reflux overnight
  2. filtrationthe reaction was filtered through celite (rinsing with methylene chloride)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-649fef579f12471193a55812df55b62c
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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