Reaction #1244263

Reaction equation

alcohol

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

Ts2O

→

12

Yield 53.1%

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

Yield 53.1%

Solvents

DCM

Conditions

Workup

1. 1
   ConcentrationThe reaction was concentrated in vacuo
2. 2
   Otherpurified on a silica gel cartridge

Procedure

To a round bottom flask containing alcohol 11 (160 mg, 0.672 mmol), TEA (136 mg, 1.34 mmol) and DCM (5 mL) was added Ts2O (263 mg, 0.806 mmol). The reaction was stirred at RT for 4 hrs. TLC indicated that the reaction was complete. The reaction was concentrated in vacuo and purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford 140 mg (53% yield) of 12 as a pale orange oil. Mass Spec (lo-res): Calc'd for C15H16N6O5S: 392.092. found: 393.10 (M+H).

Source