Potassium Carbonate → HCID 22605336, compound

HRID 2307253Notes

Reaction equation

HRID 2307253 reaction equation
[NH:1]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(#N)C>[CH2:30]([O:29][C:27](=[O:28])[CH2:26][CH2:25][CH2:24][CH2:23][N:1]1[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N:2]1)[CH3:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 142184diethyl 1H-pyrazole-3,5-dicarboxylate

Product 1

HCID 22605336HCID 22605336, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diethyl 3,5-pyrazoledicarboxylate (50 g, 0.236 mol) was dissolved in acetonitrile (500 ml) under a nitrogen atmosphere. Potassium carbonate (33 g, 0.236 mol) was added followed by ethyl 5-bromovalerate (37.7 ml, 0.235 mol) and the mixture heated under reflux for 2 hours. The solvent was removed in vacuo leaving a clear oil which was partitioned between ethyl acetate and water. The organic phase was separated and the aqueous phase further extracted with ethyl acetate (×2). The organic extracts were combined, dried (MgSO4), filtered and concentrated under reduced pressure to give 75 g of the title product.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. customleaving a clear oil which
  5. customwas partitioned between ethyl acetate and water
  6. customThe organic phase was separated
  7. extractionthe aqueous phase further extracted with ethyl acetate (×2)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-227e5f3c726a4a89ae31ec93527cfc96
Source dataset
uspto-grants-2004_12
Patent number
US06831074B2

Reaction notes

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