반응 #582482

반응 방정식

Tributyltin chloride

n-butyllithium

Tetrahydrofuran

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

→

tributyl[5-(1,3-dioxolan-2-yl)furan-2-yl]tin

수율 75.5%

용매

n-hexane

Water

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for 5 hours
2. 2
   추출extracted with ethyl acetate (50 mL)
3. 3
   건조The organic layer was dried over anhydrous sodium sulfate
4. 4
   기타the solvent was evaporated away under reduced pressure
5. 5
   기타The resulting residue was purified through silica gel column chromatography (n-hexane to ethyl acetate/n-hexane=1/20)

실험 절차

Tetrahydrofuran (10 mL) solution of 2-(1,3-dioxolan-2-yl)furan (1.0 g, 7.1 mmol) was cooled to −78° C., and n-hexane solution of 1.6 mol/L n-butyllithium (4.5 mL, 7.2 mmol) was dropwise added thereto, and stirred for 3 hours. Tributyltin chloride (2.6 g, 7.9 mmol) was dropwise added to the reaction mixture, and stirred for 5 hours with heating up to room temperature. Water (10 mL) was added to the reaction mixture, and extracted with ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through silica gel column chromatography (n-hexane to ethyl acetate/n-hexane=1/20) to obtain tributyl[5-(1,3-dioxolan-2-yl)furan-2-yl]tin (2.3 g, 75%).

출처