تفاعل #9752

معادلة التفاعل

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

المذيبات

tetrahydrofuran

diethylether

—

hexanes

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred at this temperature for 1 hour
2. 2
   workup.STIRRINGstirring
3. 3
   درجة الحرارةto warm to ambient temperature
4. 4
   استخلاصthis mixture was extracted with water
5. 5
   تجفيفthe ether layer dried with brine and over magnesium sulfate
6. 6
   أخرىThe product isolated
7. 7
   أخرىafter evaporation of the solvent
8. 8
   أخرىwas further purified by flash column chromatography

الإجراء التجريبي

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.

المصدر