Hydrofluoric Acid → Ethyl 4-methyl-1H-1,2,3-triazole-1-acetate

HRID 1947753Notes

Reaction equation

HRID 1947753 reaction equation
[CH3:1][C:2]1[N:3]=[N:4][N:5]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]=1[Si](C)(C)C.F>C1COCC1.O>[CH3:1][C:2]1[N:3]=[N:4][N:5]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=1

Participants

5

Reactant 2

HCID 14917Hydrofluoric AcidHCID 66839489Ethyl 4-methyl-5-(trimethylsilyl)-1H-1,2,3-triazole-1-acetate

Product 1

HCID 59603650Ethyl 4-methyl-1H-1,2,3-triazole-1-acetateYield 94.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.77 g (3.2 mmol) of ethyl [4-methyl-5-(trimethylsilyl)-1H-1,2,3-triazole-1-yl]acetate from step A above in 2 mL of THF was added 1.3 mL (32 mmol) of a solution of 50% hydrofluoric acid in water. The resulting mixture was stirred at room temperature for 3 h and then evaporated to dryness in vacuo. Next, 5 mL of a 2.0 N ammonia in methanol solution was added and then the mixture was again evaporated to dryness in vacuo. The mixture was dissolved in dichloromethane, filtered and then evaporated in vacuo to afford the title compound as a clear gum (0.51 g. 93%). 1HNMR (500 MHz, CDCl3) δ: 7.5 (s, 1H), 5.05 (s, 2H), 4.23 (m, 2H), 2.30 (s, 3H), 1.30 (m, 3H).

Workup

  1. customevaporated to dryness in vacuo
  2. additionNext, 5 mL of a 2.0 N ammonia in methanol solution was added
  3. customthe mixture was again evaporated to dryness in vacuo
  4. dissolutionThe mixture was dissolved in dichloromethane
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-158729e295df464492857b6151950d1a
Source dataset
uspto-grants-2013_03
Patent number
US08399480B2

Reaction notes

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