Potassium Carbonate → ethyl-5-[(4-oxotetrahydro-2H-pyran-3-yl)oxy]-1H-pyrazole-3-carboxylate

HRID 1744984Notes

Reaction equation

HRID 1744984 reaction equation
[OH:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:19]1[C:24](=[O:25])[CH2:23][CH2:22][O:21][CH2:20]1>C(#N)C>[CH2:10]([O:9][C:7]([C:4]1[CH:3]=[C:2]([O:1][CH:19]2[C:24](=[O:25])[CH2:23][CH2:22][O:21][CH2:20]2)[NH:6][N:5]=1)=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 222245413-Bromooxan-4-oneHCID 178469373HCID 178469373, compound

Product 1

HCID 178469295ethyl-5-[(4-oxotetrahydro-2H-pyran-3-yl)oxy]-1H-pyrazole-3-carboxylateYield 79.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the stirred suspension of ethyl 5-hydroxy-1H-pyrazole-3-carboxylate (7.0 g, 45 mmol) and 24.9 g g of potassium carbonate in 500 ml of acetonitrile was added 8.0 g of 3-bromo-tetrahydro-pyran-4-one, and refluxed for 16 hours. The reaction mixture was allowed to cool to room temperature, then filtered, the solid was washed with acetonitrile. The filtrate was concentrated to an oil. The residue was dissolved in ethyl acetate and extracted with water. The organic phase was dried over MgSO4 and evaporated to dryness. 9.0 g (78%) of the desired product was obtained as a white solid. M.Pt. 121–123° C.; (M+H) 255.

Workup

  1. temperaturerefluxed for 16 hours
  2. filtrationfiltered
  3. washthe solid was washed with acetonitrile
  4. concentrationThe filtrate was concentrated to an oil
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. extractionextracted with water
  7. dry with materialThe organic phase was dried over MgSO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-ce9ab4815f454567a97d239776576388
Source dataset
uspto-grants-2006_03
Patent number
US07018997B2

Reaction notes

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