Tributyl(1-ethoxyvinyl)tin

Reaction

Chemical Properties

Uses

General Description

Synthesis

1461-22-9

109-92-2

97674-02-7

Under nitrogen protection, 112 g of potassium tert-butoxide (1.0 mmol), and 139.2 g of tetramethylethylenediamine (1.2 mmol) were added to 1000 mL of anhydrous hexane and cooled to -30 °C. A 400 mL hexane solution of n-butyllithium (2.5 M) was slowly added dropwise, and the reaction was maintained at -30 °C for 1.5 h after completion of the dropwise addition, followed by cooling to -40 °C. 108 g of vinyl ether (1.5 mmol) was dissolved in 200 mL of anhydrous tetrahydrofuran and slowly added dropwise to the above mixed solution, maintained at -40 °C for 0.5 h. After the reaction was completed, it was warmed up to -20 °C to continue the reaction for 1 h. It was subsequently cooled to -78 °C. 227.9 g of tributyltin chloride (0.7 mmol) was dissolved in 500 mL of anhydrous tetrahydrofuran and slowly added dropwise to the reaction mixture, maintained at -78 °C for 2 hours, followed by natural warming and stirring for 8 hours. Upon completion of the reaction, the reaction was quenched by slow dropwise addition of 400 mL of saturated ammonium chloride solution, filtered and the organic phase was separated. The aqueous phase was extracted with hexane (500 mL x 3), the organic layers were combined and washed sequentially with water (500 mL x 3) and saturated brine (500 mL x 3). The organic phase was dried with 100 g of anhydrous sodium sulfate, filtered and concentrated under reduced pressure to constant weight to give 228.7 g of tributyl(1-ethoxyvinyl)tin crude product. The crude product was subjected to distillation under vacuum and the fraction at 75 °C-85 °C at 0.005 mmHg was collected to give 205 g of colorless transparent liquid in 81.03% yield.

References