반응 #1778532

반응 방정식

4-fluorobenzyl bromide

1,3-dioxolan-2-yl-furan

n-butyl lithium

→

title compound

수율 51.0%

2-(5-(4-Fluoro-benzyl)-furan-2-yl)-[1,3]dioxolane

수율 51.0%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGwas stirred for another hour at −78° C
2. 2
   기타partitioned into ethyl acetate
3. 3
   기타The organic layer was separated
4. 4
   세척washed with saturated aqueous sodium chloride
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   여과filtered
7. 7
   농축The filtrate was concentrated under a reduced pressure
8. 8
   기타the residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:10 to 1:3)

실험 절차

To a tetrahydrofuran (50 mL) solution of 2-(1,3-dioxolan-2-yl-furan (5 g, 35.7 mmol) was added n-butyl lithium (15.6 mL, 2.64 M hexane solution, 41.1 mmol) at −78° C., which was stirred for 1 hour at that temperature. A tetrahydrofuran solution of 4-fluorobenzyl bromide (6.9 g, 36.5 mmol) was added dropwise to this mixture, which was stirred for another hour at −78° C. The mixture was raised to room temperature and partitioned into ethyl acetate and a saturated ammonium chloride aqueous solution. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:10 to 1:3) to obtain the title compound (4.51 g, 51%).

출처