Potassium Fluoride → Dimethyl 1-methyl-1H-1,2,3-triazole-4,5-dicarboxylate

HRID 1621144Notes

Reaction equation

HRID 1621144 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[N:7][N:8]([CH:14]([Si](C)(C)C)C)[C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[O:4].[F-].[K+]>CO.C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]([C:5]1[N:6]=[N:7][N:8]([CH3:14])[C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[O:4]

Participants

5

Reactant 2

HCID 522689Potassium FluorideHCID 71279141HCID 71279141, compound

Product 1

HCID 12574370Dimethyl 1-methyl-1H-1,2,3-triazole-4,5-dicarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a solution of 1-trimethylsilanylethyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester (10 g, 36.9 mmol) in methanol (100 mL) was added potassium fluoride (11.07 g, 184.5 mmol) at RT. The reaction mixture was stirred at RT for 6 h. After solvent removal in vacuo, the crude material was diluted with water (100 mL) and extracted with ethyl acetate (2×150 mL). The combined organic layer was washed with water (2×50 mL) and brine (50 mL), dried over anhydrous Na2SO4, filtered, and evaporated in vacuo. The product was obtained after purification by flash chromatography (using silica gel and 30% ethyl acetate/hexane) as white solid (4.3 g, 21.6 mmol, 58.5%).

Workup

  1. customAfter solvent removal in vacuo
  2. additionthe crude material was diluted with water (100 mL)
  3. extractionextracted with ethyl acetate (2×150 mL)
  4. washThe combined organic layer was washed with water (2×50 mL) and brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe product was obtained

Sources & evidence

ORD record
ord-29794cbe2f7948b18ff4517edee2f019
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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