Methanol → HCID 57600007, compound

HRID 1787452Notes

Reaction equation

HRID 1787452 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]=[N+:12]=[N-:13])[CH:5]=1.[C:15]([O:19][Si](C)(C)C)(=[O:18])[C:16]#[CH:17].CO>O>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N:11]2[CH:17]=[C:16]([C:15]([OH:19])=[O:18])[N:13]=[N:12]2)[CH:5]=1)=[O:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 5156487HCID 5156487, compoundHCID 57600002HCID 57600002, compound

Product 1

HCID 57600007HCID 57600007, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Azido-4-methyl-benzoic acid methyl ester (878 mg, 4.60 mmol) and trimethylsilyl propiolate (777 mg, 5.05 mmol) were heated to 80° C. in a sealed tube overnight. The tube was cooled and the contents were mixed with 20 mL of MeOH. After 2 h, the mixture was poured into rapidly stirring cold water, and the resulting precipitate was filtered and dried under air to provide 823 mg of 1-(5-Methoxycarbonyl-2-methyl-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid.

Workup

  1. temperatureThe tube was cooled
  2. additionthe mixture was poured
  3. filtrationthe resulting precipitate was filtered
  4. customdried under air

Sources & evidence

ORD record
ord-43d78069d0b5457bad2184ea626468e0
Source dataset
uspto-grants-2009_03
Patent number
US07511042B2

Reaction notes

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