Propargyl alcohol → (1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methanol

HRID 2103954Notes

Reaction equation

HRID 2103954 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH2:13]([OH:16])[C:14]#[CH:15]>C(O)(C)(C)C.O.O>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][N:1]2[CH:15]=[C:14]([CH2:13][OH:16])[N:3]=[N:2]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 109317671-(Azidomethyl)-4-methoxybenzene

Product 1

HCID 23139019(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methanolYield 59.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

93 mmol 1-(azidomethyl)-4-methoxybenzene, 110 mmol propargyl alcohol were mixed in 230 ml tert-butyl alcohol/H2O (1:1) solution. 1 mmol CuSO4.5H2O and 10 mmol Ascorbic acid sodium salts dissolved in 2 ml water were added into the solution. The mixture was stirred for 2 days. After evaporation, the mixture was purified by flash column to give 55 mmol (1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-yl) methanol. 1H NMR (CDCl3): 7.42 (1H, s), 7.22 (2H, d, JH-H=8.70), 6.88 (2H, d, JH-H=8.70), 5.43 (2H, s), 4.73 (2H, s), 3.79 (3H, s).

Workup

  1. additionwere added into the solution
  2. customAfter evaporation
  3. customthe mixture was purified by flash column

Sources & evidence

ORD record
ord-22ee028bb8004d0188827e29e409a097
Source dataset
uspto-grants-2009_08
Patent number
US07576165B2

Reaction notes

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