1-Pentyne → 4-(4-propyl-1H-1,2,3-triazol-1-yl)pyridine

HRID 1401375Notes

Reaction equation

HRID 1401375 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH:10]#[C:11][CH2:12][CH2:13][CH3:14].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>S([O-])([O-])(=O)=O.[Cu+2].O.CC(C)=O>[CH2:12]([C:11]1[N:3]=[N:2][N:1]([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=2)[CH:10]=1)[CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 123091-PentyneHCID 113324494-AzidopyridineHCID 23667548Sodium Ascorbate2×

Product 1

HCID 1177228634-(4-propyl-1H-1,2,3-triazol-1-yl)pyridine

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

4-azidopyridine (4.65 g, 38.7 mmol) and pent-1-yne (4.12 ml, 41:8 mmol) were added into a 250 mL round-bottom flask with 50 mL mixture of water/acetone. Copper(II) sulfate (0.06 g, 0.376 mmol) and sodium L-ascorbate (0.26 g, 1.292 mmol) were added to this solution and the reaction was stirred at room temperature for 24 hours. Additional sodium ascorbate (0.10 g) was added. The solution was filtered and concentrated. Ethyl acetate (200 ml) was added to the concentrated solution. The organic layer was washed twice with 25 mL water, dried with MgSO4, filtered, concentrated and dried in vacuo, producing 4-(4-propyl-1H-1,2,3-triazol-1-yl)pyridine.

Workup

  1. filtrationThe solution was filtered
  2. concentrationconcentrated
  3. additionEthyl acetate (200 ml) was added to the concentrated solution
  4. washThe organic layer was washed twice with 25 mL water
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-6842423091b64f82bbf896ffa3666792
Source dataset
uspto-grants-2014_12
Patent number
US08907105B1

Reaction notes

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