Methanol → HCID 54077336, compound

HRID 653827Notes

Reaction equation

HRID 653827 reaction equation
S(=O)(=O)(O)O.[CH3:6][OH:7].[CH2:8]([O:15][C:16]1[C:17]([CH3:25])=[N:18][N:19]([CH3:24])[C:20]=1[CH2:21][C:22]#N)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH2:26]>>[CH2:8]([O:15][C:16]1[C:17]([CH3:25])=[N:18][N:19]([CH3:24])[C:20]=1[CH2:21][C:22]([O:7][CH3:6])=[O:26])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 19890291HCID 19890291, compound

Product 1

HCID 54077336HCID 54077336, compoundYield 33%

Procedure

Concentrated sulfuric acid was added to a solution of methanol (9.5 ml) and water (0.5 ml) under ice-cooling, and (4-benzyloxy-1,3-dimethylpyrazol-5-yl)acetonitrile (1.6 g, 6.6 mmol) was added thereto and the resulting mixture was heated for 6 hours under reflux. It was then concentrated in vacuo to remove methanol. The residue was diluted with ethyl acetate, successively washed with water, aqueous sodium bicarbonate, water, and saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was chromatographed over silica gel (eluent; ethyl acetate/n-hexane=1:2) to obtain methyl (4-benzyloxy-1,3-dimethyl-pyrazol-5-yl)acetate (0.6 g, 2.2 mmol, 33%).

Workup

  1. temperaturecooling
  2. temperaturethe resulting mixture was heated for 6 hours
  3. temperatureunder reflux
  4. concentrationIt was then concentrated in vacuo
  5. customto remove methanol
  6. additionThe residue was diluted with ethyl acetate
  7. washsuccessively washed with water, aqueous sodium bicarbonate, water, and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was chromatographed over silica gel (eluent; ethyl acetate/n-hexane=1:2)

Sources & evidence

ORD record
ord-9f3e65328c16440d8ee768edb4f356ae
Source dataset
uspto-grants-1992_07
Patent number
US05128481

Reaction notes

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