Acetic Acid → HCID 15550515, compound

HRID 1386628Notes

Reaction equation

HRID 1386628 reaction equation
[CH3:1][C:2]1[C:10]([C:11](=[O:14])[CH2:12][CH3:13])=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:15](=O)([O:18]C)[O:16][CH3:17].[H-].[Na+].C(O)(=O)C>O>[CH3:13][CH:12]([C:11]([C:10]1[C:2]([CH3:1])=[N:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12)=[O:14])[C:15]([O:16][CH3:17])=[O:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 15550514HCID 15550514, compound

Product 1

HCID 15550515HCID 15550515, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2-Methyl-3-propionylpyrazolo[1,5-a]pyridine (5.28 g) was dissolved into dimethyl carbonate (100 ml), and, after adding sodium hydride (3.37 g), the mixture was refluxed for 8 hours under heat. Under cooling in water bath, acetic acid was added, then, following dilution with water, the mixture was extracted with methylene chloride. After the organic layer was dried over anhydrous sodium sulfate, solvent was distilled off under reduced pressure and the residue was purified by means of silica gel column chromatography (developing solvent, ethyl acetate:n-hexane=1:3˜1:1) to obtain aimed product (5.13 g) as a yellow oily product.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. temperatureunder heat
  3. extractionthe mixture was extracted with methylene chloride
  4. dry with materialAfter the organic layer was dried over anhydrous sodium sulfate, solvent
  5. distillationwas distilled off under reduced pressure
  6. customthe residue was purified by means of silica gel column chromatography (developing solvent, ethyl acetate:n-hexane=1:3˜1:1)

Sources & evidence

ORD record
ord-9aeb429882864ce3bdf3e704199e496a
Source dataset
uspto-grants-2001_07
Patent number
US06265577B1

Reaction notes

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