반응 #819375

반응 방정식

ammonium chloride

n-butyl lithium hexane

triethyl 2-fluoro-2-phosphonoacetate

4-benzyloxybenzaldehyde

→

title compound

수율 81.0%

ethyl (2Z)-3-[4-(benzyloxy)phenyl]-2-fluoroacrylate

수율 81.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe obtained mixture was stirred at room temperature for 3 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 (ethyl acetate:hexane=3:97-20:80)

실험 절차

A solution of triethyl 2-fluoro-2-phosphonoacetate (4.90 g, 20.2 mmol) in tetrahydrofuran (40 mL) was stirred under a nitrogen atmosphere at 0° C., and 1.6 M n-butyl lithium/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-benzyloxybenzaldehyde (4.29 g, 20.2 mmol) in tetrahydrofuran (20 mL) was added dropwise. The obtained mixture was stirred at room temperature for 3 hr and ice-cooled aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. 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 (ethyl acetate:hexane=3:97-20:80) to give the title compound (4.90 g, yield 81%) as a yellow oil.

출처