Tributyltin Chloride → Tributyl(2,3-dihydrofuran-5-yl)stannane

Participants

Reaction Conditions

Reaction Steps

A solution of 2,3-dihydrofuran (10.7 mL, 141 mmol) in anhyd THF (80 mL) was cooled to −60° C. A solution of t-BuLi (1.7 M in pentane, 100 mL, 170 mmol) was added dropwise. The yellow solution was stirred at −60° C. for 10 min then at 0° C. for 50 min. The reaction mixture was cooled down to −60° C. and Bu3SnCl (52.7 mL, 185 mmol) was added dropwise to give a colorless solution that was stirred at 0° C. for 90 min. Sat. aq NH4Cl was added dropwise and the reaction mixture was extracted with Et2O. The aqueous phase was further extracted with Et2O and the combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was distilled under 24 mbar vacuum at 150° C. and the residue was distilled again under 22 mbar vacuum at 154° C. to yield the title compound (55 g, 100%) as a light yellow liquid.

Provenance & Evidence