반응 #2167281

반응 방정식

ammonium chloride

n-Butyl lithium

2-(1,3-dioxolan-2-yl)furan

3-fluorobenzyl bromide

→

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

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGwhich was then stirred for 1 hour at −78° C.
2. 2
   workup.WAITfor 1.25 hours at room temperature
3. 3
   추출was extracted with diethyl ether
4. 4
   세척The organic layer was washed with brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   농축concentrated in vacuo
7. 7
   기타The obtained residue was purified by silica gel chromatography (hexane-ethyl acetate)
8. 8
   workup.ADDITIONa mixture of the title compound and 2-(1,3-dioxolane-2-yl)furan (8033 mg), which
9. 9
   기타was obtained

실험 절차

n-Butyl lithium (2.66M hexane solution, 25.5 mL, 67.88 mmol) was added dropwise to a solution of 2-(1,3-dioxolan-2-yl)furan (8272 mg, 59.03 mmol) in tetrahydrofuran (160 mL) that had been cooled to −78° C. solution under nitrogen atmosphere, which was then stirred for 10 minutes. To this solution was added a solution of 3-fluorobenzyl bromide (14.50 g, 76.73 mmol) in tetrahydrofuran (60 mL) dropwise, which was then stirred for 1 hour at −78° C., and for 1.25 hours at room temperature. An aqueous solution of saturated ammonium chloride was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and then, concentrated in vacuo. The obtained residue was purified by silica gel chromatography (hexane-ethyl acetate), and a mixture of the title compound and 2-(1,3-dioxolane-2-yl)furan (8033 mg), which is the starting material, was obtained.

출처