반응 #600879

반응 방정식

Magnesium

1,2-dibromoethane

8-nitroquinoline-7-carbaldehyde

8-nitro-quinoline-7-carbaldehyde

2-(5-bromo-2-fluoro-phenyl)-[1,3]dioxolane

→

title compound

수율 74.0%

(3-[1,3]Dioxolan-2-yl-4-fluoro-phenyl)-(8-nitro-quinolin-7-yl)-methanol

수율 74.0%

용매

THF

THF

반응 조건

후처리

1. 1
   온도the mixture was heated at 40° C. for 2 h
2. 2
   온도to cool to room temperature
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature for 30 min
4. 4
   기타The mixture was quenched with sat. NH4Cl (10 ml)
5. 5
   추출the aqueous phase was extracted with EtOAc (20 ml)
6. 6
   세척The organic phase was washed with brine (10 ml)
7. 7
   건조dried (Na2SO4)
8. 8
   농축concentrated in vacuo
9. 9
   기타The crude residue was purified by column chromatography with heptane/EtOAc (50:50) as the eluent

실험 절차

Magnesium (983 mg, 40.5 mmol) was suspended in anhydrous THF (30 ml). 1,2-dibromoethane (0.17 ml, 2.02 mmol) was added and the solution was stirred at room temperature for 20 min. 2-(5-bromo-2-fluoro-phenyl)-[1,3]dioxolane 417 (3.2 g, 12.95 mmol) was added dropwise and the mixture was heated at 40° C. for 2 h. The mixture was allowed to cool to room temperature. The Grignard reagent (0.43M; 28.6 ml) was added to a suspension of 8-nitroquinoline-7-carbaldehyde 204 (2.5 g, 12.4 mmol) in dry THF (30 ml) at 0° C. under a nitrogen atmosphere. The mixture was stirred at room temperature for 30 min. The mixture was quenched with sat. NH4Cl (10 ml) and the aqueous phase was extracted with EtOAc (20 ml). The organic phase was washed with brine (10 ml), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAc (50:50) as the eluent to give the title compound (3.39 g, 74%).

출처