Reaktion #9752

Reaktionsgleichung

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

Lösungsmittel

tetrahydrofuran

diethylether

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at this temperature for 1 hour
2. 2
   workup.STIRRINGstirring
3. 3
   Temperaturto warm to ambient temperature
4. 4
   Extraktionthis mixture was extracted with water
5. 5
   Trocknenthe ether layer dried with brine and over magnesium sulfate
6. 6
   SonstigeThe product isolated
7. 7
   Sonstigeafter evaporation of the solvent
8. 8
   Sonstigewas further purified by flash column chromatography

Vorschrift

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.

Quelle