Reaction #1244262

Reaction equation

sodium ascorbate

nitropropyne

2-Nitro-1-(prop-2-ynyl)-1H-imidazole

azido ethanol

→

11

Yield 76.3%

2-(4-((2-Nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)ethanol

Yield 76.3%

Solvents

MeOH

Conditions

Workup

1. 1
   workup.ADDITIONthe reaction was poured onto EtOAc
2. 2
   Washwashed with NH4OH
3. 3
   Otherthe residue was purified on a combiflash system

Procedure

To a round bottom flask was added nitropropyne 10 (150 mg, 0.99 mmol) and azido ethanol (86 mg, 0.99 mmol). To this flask was added CuSO4 (0.04M, 100 uL) and sodium ascorbate (0.1 M, 100 uL). After 16 hrs, the reaction was poured onto EtOAc and washed with NH4OH. The organics were combined and the residue was purified on a combiflash system using EtOAc:Hex as the eluent followed by DCM:MeOH to afford 180 mg (76.3% yield) of 11 as a clear colorless oil. Mass Spec (lo-res): Calc'd for C8H10N6O3: 238.08; found: 239.10 (M+H).

Source