1-benzyl-1H-1,2,3-triazole-4-carbaldehyde synthesis

7synthesis methods

Product Name:1-benzyl-1H-1,2,3-triazole-4-carbaldehyde
CAS Number:124940-34-7
Molecular formula:C10H9N3O
Molecular Weight:187.2

10160-87-9
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100-39-0
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1-benzyl-1H-1,2,3-triazole-4-carbaldehyde

124940-34-7
20 suppliers
$110.00/50mg

Yield: 67%

Reaction Conditions:

with sodium azide;copper(II) sulfate;sodium L-ascorbate in water;tert-butyl alcohol at 70; for 24 h;

Steps:

S.3 General procedure for tandem substitution/deprotection/CuAAC.
General procedure: To a 20 mL screw-top vial was added (in order) CuSO₄ (0.032 g, 0.2 mmol), L-ascorbic acid sodium salt (0.079 g, 0.4 mmol), NaN₃ (0.065 g, 1.0 mmol), water (5 mL), t-butyl alcohol (5 mL), organic bromide reactant (1.0 mmol) and propargyl aldehyde diethyl acetal (0.158 mL, 1.1 mmol). The vial was then capped and stirred at either room temperature or 70 °C for 24 h. The reaction mixture was then extracted between CH₂Cl₂ and 5% NH₄OH (aq). The organic layer was separated, dried with MgSO₄ and gravity filtered. The solvent was removed via rotary evaporation to give the isolated product or product mixture used for NMR analysis. Further purification was accomplished by silica gel chromatography using either CH₂CH₂ or 20:1 CH₂CH₂:ethyl acetate eluent.

References:

Fletcher, James T.;Christensen, Joseph A.;Villa, Eric M. [Tetrahedron Letters,2017,vol. 58,# 47,p. 4450 - 4454] Location in patent:supporting information