Reaction #167823

Reaction equation

azidomethyl pivalate

butanol water

5-(prop-2-ynyloxy)-2-(1H-tetrazol-1-yl)pyridine

sodium ascorbate

→

expected product

(4-((6-(1H-Tetrazol-1-yl)pyridin-3-yloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl pivalate

Solvents

water

water

Water

Conditions

Workup

1. 1
   Extractionthe suspension was extracted with ethyl acetate
2. 2
   OtherThe organic layer was separated
3. 3
   Dryingdried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo

Procedure

To a solution of azidomethyl pivalate (4.26 g, 27.1 mmol) in 1:1 text -butanol water (90 mL total) was added 5-(prop-2-ynyloxy)-2-(1H-tetrazol-1-yl)pyridine (5.45 g, 27.1 mmol), sodium ascorbate (1.4 mL of a 1M solution in water) and copper sulfate (1.4 mL of a 1M solution in water). The solution was stirred at room temperature for 72 hours. Water was added and the suspension was extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to afford the expected product which was used in the next step without further purification. 1H NMR (DMSO-d6): δ 10.07 (1H, s), 8.43-8.41 (2H, m), 8.00 (1H, d, J=8.8 Hz), 7.88 (1H, dd, J=3.2, 8.8 Hz), 6.32 (2H, s), 5.38 (2H, s), 1.08 (9H, s).

Source