Reaktion #2015774

Reaktionsgleichung

azidomethyl pivalate

tert-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

Lösungsmittel

water

water

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe suspension was extracted with ethyl acetate
2. 2
   SonstigeThe organic layer was separated
3. 3
   Trocknendried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo

Vorschrift

To a solution of azidomethyl pivalate (4.26 g, 27.1 mmol) in 1:1 tert-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).

Quelle