HCID 22224442, compound → HCID 22224531, compound

HRID 1744987Notes

Reaction equation

HRID 1744987 reaction equation
[N:1]1[N:8]2[C:4]([O:5][C:6]3[CH2:12][O:11][CH2:10][CH2:9][C:7]=32)=[CH:3][C:2]=1[CH2:13][OH:14]>C(Cl)(Cl)Cl.O=[Mn]=O>[N:1]1[N:8]2[C:4]([O:5][C:6]3[CH2:12][O:11][CH2:10][CH2:9][C:7]=32)=[CH:3][C:2]=1[CH:13]=[O:14]

Participants

4

Reactant 1

HCID 22224442HCID 22224442, compound

Product 1

HCID 22224531HCID 22224531, compoundYield 80.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6212ChloroformSolvent

Procedure

To the stirred solution of 7,8-dihydro-5H-pyrano[4,3-d]pyrazolo[5,1-b][1,3]oxazol-2-ylmethanol (1.0 g, 5.1 mmol) in 60 ml of CHCl3 was added 8 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. 0.79 g of the product was obtained (80%); (M+H) 193

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-30a503f7a23b4e8c98e306d7fb31e134
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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