Pyrazolo[5,1-b]oxazole-6-methanol, 2,3-dihydro- → 2,3-Dihydropyrazolo(5,1-b)oxazole-6-carboxaldehyde

HRID 2216619Notes

Reaction equation

HRID 2216619 reaction equation
[O:1]1[CH2:5][CH2:4][N:3]2[N:6]=[C:7]([CH2:9][OH:10])[CH:8]=[C:2]12>CCl.O=[Mn]=O>[O:1]1[CH2:5][CH2:4][N:3]2[N:6]=[C:7]([CH:9]=[O:10])[CH:8]=[C:2]12

Participants

4

Reactant 1

HCID 21941355Pyrazolo[5,1-b]oxazole-6-methanol, 2,3-dihydro-

Product 1

HCID 219414832,3-Dihydropyrazolo(5,1-b)oxazole-6-carboxaldehydeYield 84.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6327Methyl ChlorideSolvent

Procedure

To the stirred solution of 2,3-dihydropyrazolo[5,1-b][1,3]oxazole-6-methanol (2.60 g, 18.5 mmol) in 60 ml of CH3Cl was added 12.9 g of MnO2. Th suspension was refluxed for 1.5 hour under a nitrogen atmosphere. The reaction mixture was filtered through a pad of Celite. The filtrate was concentrated to give yellow oil. The product was purified by chromatography. 2.15 g of the product was obtained (84.3%).

Workup

  1. temperatureTh suspension was refluxed for 1.5 hour under a nitrogen atmosphere
  2. filtrationThe reaction mixture was filtered through a pad of Celite
  3. concentrationThe filtrate was concentrated
  4. customto give yellow oil
  5. customThe product was purified by chromatography

Sources & evidence

ORD record
ord-a4b082610f174d91a8041bbd1b0ab1bd
Source dataset
uspto-grants-2006_09
Patent number
US07112582B2

Reaction notes

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