HCID 68685932, compound → HCID 21941447, compound

HRID 1158898Notes

Reaction equation

HRID 1158898 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:11][N:5]2[N:6]=[C:7]([CH2:9][OH:10])[CH:8]=[C:4]2[CH2:3]1>C(Cl)(Cl)Cl.O=[Mn]=O>[CH3:1][C:2]1([CH3:12])[CH2:11][N:5]2[N:6]=[C:7]([CH:9]=[O:10])[CH:8]=[C:4]2[CH2:3]1

Participants

4

Reactant 1

HCID 68685932HCID 68685932, compound

Product 1

HCID 21941447HCID 21941447, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

To 3.19 g of the crude (5,5-dimethyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)methanol in 222 mL of CHCl3 was added activated MnO2 (18.5 g) under a nitrogen atmosphere at room temperature, and then refluxed for 1 h. The mixture was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. The residue was applied to silica-gel column chromatography, and then the column was eluted with hexane-AcOEt (3:1). The titled compound was obtained as a brown solid (2.48 g, 68.0% from the ester).

Workup

  1. temperaturerefluxed for 1 h
  2. filtrationThe mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washthe column was eluted with hexane-AcOEt (3:1)

Sources & evidence

ORD record
ord-144351519f6e458ab00717c538f0314c
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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