反应详情

温度

24 °C

The tetrazoleacetic acid, ethyl ester (50 g, 0.26 tool) obtained in (a) was suspended in acetonitrile (600 mL) and triethylamine (52.4 g, 0.52 tool)was added in one portion. The solution was heated at reflux for 5 minutes, cooled to 24° C., and then treated dropwise with 1-bromododecane (64.5 g, 0.26 mol). The solution was refluxed overnight, cooled, and the solvent concentrated in vacuo. The residue was triturated with ethyl acetate (300 mL), filtered, and the filtrate was washed with aqueous HCl (1M), brine, dried (MgSO4), and filtered. The filtrate was concentrated in vacuo leaving a viscous liquid. The 2-isomer was separated from the crude mixture using silica gel chromatography (elution with 25% EtOAc/75% hexane), isolating 2-dodecyltetrazoleacetic acid, ethyl ester (41.8 g, 49%) as a pale yellow liquid.

1. temperatureThe solution was heated
2. temperatureat reflux for 5 minutes
3. temperatureThe solution was refluxed overnight
4. temperaturecooled
5. concentrationthe solvent concentrated in vacuo
6. customThe residue was triturated with ethyl acetate (300 mL)
7. filtrationfiltered
8. washthe filtrate was washed with aqueous HCl (1M), brine
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. concentrationThe filtrate was concentrated in vacuo
12. customleaving a viscous liquid
13. customThe 2-isomer was separated from the crude mixture
14. washsilica gel chromatography (elution with 25% EtOAc/75% hexane)