Reaction #964558

Reaction equation

(azidomethyl)(trimethyl)silane

3,3-diethoxyprop-1-yne

sodium

BuOH H2O

→

crude title compound

Yield 81.3%

4-(Diethoxymethyl)-1-[(trimethylsilyl)methyl]-1H-1,2,3-triazole

Yield 81.3%

Solvents

water

Conditions

Workup

1. 1
   OtherTo a 100 ml round bottom flask equipped with a magnetic stir bar
2. 2
   Extractionextracted with EtOAc
3. 3
   WashThe combined organic layers were washed with brine
4. 4
   Dryingdried over anhydrous Na2SO4
5. 5
   Filtrationfiltered
6. 6
   ConcentrationThe filtrate was concentrated in vacuum

Procedure

To a 100 ml round bottom flask equipped with a magnetic stir bar were added (azidomethyl)(trimethyl)silane (1.000 g, 7.740 mmol), 3,3-diethoxyprop-1-yne (0.992 g, 7.740 mmol), freshly made 1.0N sodium asorbate (0.774 ml, 7.740 mmol), and 1.0N Cu2SO4 (0.774 ml, 7.740 mmol) into 30.0 ml of a mixed solvent BuOH/H2O (1:1). The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum to give the crude title compound as a light yellow liquid (1.620 g, 81% crude). ES-MS [M+1]+: 258.1 (M+H). This intermediate was carried over to the next step without further purifications and characterizations.

Source