반응 #595111

반응 방정식

ammonium chloride

n-butyllithium hexane

ethyl diethylphosphono-2-fluoroacetate

4-nitrobenzaldehyde

→

title compound

수율 72.0%

ethyl(2Z)-2-fluoro-3-(4-nitrophenyl)acrylate

수율 72.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at room temperature for 16 hr
2. 2
   workup.ADDITIONwas added
3. 3
   추출The mixture was extracted with ethyl acetate
4. 4
   세척the extract was washed with saturated brine
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by silica gel column chromatography (3%-40% ethyl acetate/hexane)

실험 절차

A solution of ethyl diethylphosphono-2-fluoroacetate (4.90 g, 20.2 mmol) in tetrahydrofuran (40 mL) was stirred under a nitrogen atmosphere at 0° C. and 1.6 M n-butyllithium/hexane solution (13.1 mL, 21.0 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 30 min, and a solution of 4-nitrobenzaldehyde (3.05 g, 20.2 mmol) in tetrahydrofuran (40 mL) was added dropwise. The mixture was stirred at room temperature for 16 hr, and ice-cooled aqueous ammonium chloride solution was added. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (3%-40% ethyl acetate/hexane) to give the title compound (3.46 g, yield 72%) as a yellow powder.

출처