HCID 21941394, compound → HCID 21941405, compound

HRID 2216604Notes

Reaction equation

HRID 2216604 reaction equation
[O:1]1[C:5]([CH2:6][OH:7])=[CH:4][C:3]2[CH2:8][CH2:9][CH2:10][C:2]1=2>O=[Mn]=O.C(Cl)(Cl)Cl>[O:1]1[C:5]([CH:6]=[O:7])=[CH:4][C:3]2[CH2:8][CH2:9][CH2:10][C:2]1=2

Participants

4

Reactant 1

HCID 21941394HCID 21941394, compound

Product 1

HCID 21941405HCID 21941405, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

Activated MnO2 (9.3 g) was added to the CHCl3 (135 mL) solution of (5,6-dihydro-4H-cyclopenta[b]furan-2-yl)methanol (1.86 g) and refluxed for 1 h under a nitrogen atmosphere. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with n-hexane-AcOEt (9/1–7/1). The titled compound was obtained as yellow crystals (1.51 g, 77%).

Workup

  1. temperaturerefluxed for 1 h under a nitrogen atmosphere
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washthe column was eluted with n-hexane-AcOEt (9/1–7/1)

Sources & evidence

ORD record
ord-1deaa0d6043446ada8b7253771ab17dc
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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