Tributylstannane → Tributyl(3,3,3-trifluoroprop-1-en-2-yl)stannane

Participants

Reaction Conditions

Reaction Steps

A 2M solution of LDA in tetrahydrofuran (7.5 ml, 15 mmole) was added to tetrahydrofuran (5 ml) at −5° C. To this solution was added tri-n-butylstannane (4.36 g, 15 mmole) dropwise and the mixture was left to stir for 20 min. In a second flask, copper(I)iodide (1.43 g, 7.5 mmoles) was suspended in tetrahydrofuran (5 ml). The flask was cooled to −10° C. and the lithium tri-n-butylstannane solution was then transferred dropwise via a syringe to the copper(I)iodide suspension. The mixture was stirred at −10° C. for 0.5 h, cooled to −78° C. then treated dropwise with 2-bromotrifluoropropene (1.32 g, 7.5 mmole). Stirring was continued for a further 0.5 h followed by 1 h at room temperature. Volatiles were removed in vacuo and the residue was dissolved in ether (100 ml), filtered and the solvent was removed to give an oil. Purification was by distillation. The fraction boiling at 114° C./4.6 mbar was collected to give the title compound (2.16 g, 75%).

Provenance & Evidence