Tributyltin Chloride → 2-(Diethoxymethyl)-5-(tributylstannyl) thiophene

Participants

Reaction Conditions

Reaction Steps

18.6 g (100 mmol) of 2-(diethoxymethyl) thiophene in 100 ml of tetrahydrofuran ("THF") was placed in a 2-neck flask equipped with dropping funnel. The solution was cooled to -78° C. under nitrogen atmosphere and added 62.5 mL of 1.6 M n-butyl lithium (100 mmol) dropwise through dropping funnel in 1 hr. The reaction mixture was stirred at -78° C. for 1 hr and gradually warmed up to room temperature. After stirred for 30 minutes, the mixture was again cooled to -78° C. and added dropwise a THF (50 mL) solution of 32.5 g (100 mmol) of tributyl tin chloride with continual stirring. Gradually warmed up to room temperature, the mixture was stirred for another 10-12 hrs at room temperature and then concentrated. Reduced pressure distillation yielded 36.8 g (80%) of 2-(diethoxymethyl)-5-(tributylstannyl) thiophene (bp 195° C./1 torr).

Provenance & Evidence