반응 #9752

반응 방정식

tributyltin chloride

2-(3-methylthien-2-yl)-1,3-dioxolane

intermediate 75

2-(3-methylthien-2-yl)-1,3-dioxolane

n-butyl lithium

→

title compound

tributyl[5-(1,3-dioxolan-2-yl)-4-methylthien-2-yl]stannane

용매

tetrahydrofuran

diethylether

—

hexanes

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred at this temperature for 1 hour
2. 2
   workup.STIRRINGstirring
3. 3
   온도to warm to ambient temperature
4. 4
   추출this mixture was extracted with water
5. 5
   건조the ether layer dried with brine and over magnesium sulfate
6. 6
   기타The product isolated
7. 7
   기타after evaporation of the solvent
8. 8
   기타was further purified by flash column chromatography

실험 절차

A mixture of 2-(3-methylthien-2-yl)-1,3-dioxolane (intermediate 75, 1.5 g) in tetrahydrofuran (50 ml), stirred at −60° C. under a nitrogen atmosphere, was treated drop-wise with 1.6M n-butyl lithium in hexanes (6.1 ml). The reaction mixture was stirred at this temperature for 1 hour and tributyltin chloride (2.6 ml) was added; stirring was continued at −60° C. for 1 hour and then the reaction allowed to warm to ambient temperature. After 18 hours the reaction mixture was diluted with diethylether and this mixture was extracted with water and the ether layer dried with brine and over magnesium sulfate. The product isolated after evaporation of the solvent was further purified by flash column chromatography using cyclohexane:ethyl acetate (50:1) as eluent to give the title compound as a yellow oil.

출처