Reaktion #720761

Reaktionsgleichung

sodium ethanolate

ethanol

mixture

2-bromo-1-(cyclopropylmethoxy)-3-nitrobenzene

ethyl 2-azidoacetate

→

title compound

Ausbeute 28.0%

(Z)-ethyl 2-azido-3-(2-bromo-3-(cyclopropylmethoxy)phenyl)acrylate

Ausbeute 28.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesealed
2. 2
   workup.ADDITIONpoured into a separatory funnel
3. 3
   Extraktionextracted from 100 mL water with 3×100 mL ether
4. 4
   WaschenThe combined organics were washed with saturated aqueous sodium chloride
5. 5
   Trocknendried over magnesium sulfate
6. 6
   FiltrationAfter filtration and solvent removal the residues
7. 7
   Sonstigewere chromatographed on a 60 g silica cartridge
8. 8
   Wascheneluting with 0-10-100% ethyl acetate/heptane

Vorschrift

A 50 mL roundbottom flask with stirbar was charged with sodium ethanolate, 21 wt % in ethanol (14 mL, 37.6 mmol), sealed and cooled to −20° C. under nitrogen. A mixture of Example 99A (6.38 g, 25.01 mmol) and ethyl 2-azidoacetate (10 g, 77 mmol) were added dropwise over 15 minutes. The solution was stirred for 3.5 hours, then poured into a separatory funnel and extracted from 100 mL water with 3×100 mL ether. The combined organics were washed with saturated aqueous sodium chloride, dried over magnesium sulfate. After filtration and solvent removal the residues were chromatographed on a 60 g silica cartridge eluting with 0-10-100% ethyl acetate/heptane to provide 2.56 g (28%) of the title compound.

Quelle