Tributyltin Chloride → Trimethyl((tributylstannyl)ethynyl)silane

Participants

Reaction Conditions

Reaction Steps

n-BuLi (1.6 M, 24.4 mL, 39 mmol) was added dropwise to a solution of ethynyltrimethylsilane (4.0 g, 41 mmol) in THF (40 mL) at −78° C. and gradually warmed to 0° C. over 30 min. The reaction mixture was cooled to −78° C. again and tributyltin chloride (11.4 mL, 39 mmol) in THF (30 mL) was added dropwise to the resultant mixture. The reaction mixture was stirred for 18 h at room temperature and quenched with water (20 mL). The mixture was extracted with diethyl ether (2×100 mL) and the combined organic extracts were washed with brine (50 mL). The organic phase was dried and concentrated to give yellow oil (15.0 g, 95%), which was used directly in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 1.67-1.45 (m, 6H), 1.45-1.20 (m, 6H), 0.98 (t, 6H, J=8.4 Hz), 0.90 (t, 9H, J=7.2 Hz), 0.16 (s, 9H).

Provenance & Evidence