Reaktion #10374

Reaktionsgleichung

3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid

ethanol

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

title compound

Ausbeute 53.3%

3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid ethyl ester

Ausbeute 53.3%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITroom temperature for 21 hours
2. 2
   Sonstigethe solvents are evaporated
3. 3
   workup.DISSOLUTIONThe residue is dissolved in chloroform
4. 4
   Waschenwashed with saturated NaHCO3 and brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigePurification by chromatography (1:8 ethyl acetate/hexanes)

Vorschrift

3-(Benzyloxyiminomethyl)-2,4,5-trifluorobenzoic acid (0.117 g, 0.378 mmol), 4-dimethylaminopyridine (0.023 g, 0.189 mmol), anhydrous ethanol (0.030 mL, 0.517 mmol) are mixed in dichloromethane (6 mL), cooled to 0° C., and treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.082 g, 0.427 mmol). After 2 hours at 0° C. and room temperature for 21 hours, the solvents are evaporated. The residue is dissolved in chloroform, washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification by chromatography (1:8 ethyl acetate/hexanes) provided the title compound (0.068 g). 1H NMR (200 MHz, CDCl3): δ 8.27 (s, 1H), 7.87–7.66 (m, 1H), 7.49–7.28 (m, 5H), 5.27 (s, 2H), 4.48–4.29 (q, 2H), 1.46–1.31 (t, 3H).

Quelle