Reaction #454041

Reaction equation

n-Butyllithium

3,4-(ethylenedioxy)thiophene

Tributylstannyl chloride

→

2-(tributylstannyl)-3,4-(ethylenedioxy)thiophene

Yield 98.0%

Solvents

THF

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   FiltrationAt room temperature the mixture was filtered
3. 3
   Otherdried

Procedure

n-Butyllithium (77 mL, 192.5 mmol, 2.5 M solution in hexane) was added dropwise at -78° C. to a solution of 3,4-(ethylenedioxy)thiophene (25 g, 175.9 mmol) in anhydrous THF (100 mL) under nitrogen. The solution was stirred for 1 h and warmed to -40° C. Tributylstannyl chloride (85.89 g, 263.9 mmol) was added and the entire solution was finally allowed to warm to room temperature. At room temperature the mixture was filtered using Celite and the solvent was stripped. The organo-tin compound was vacuum dried to give 2-(tributylstannyl)-3,4-(ethylenedioxy)thiophene, obtained as a dark yellow liquid, yield=98%. MS(EI) m/z (rel int): 375 [(M)+ --C4H8, 100%] and 319[(M)+ --C8H16, 18%].

Source