Trimethyltin chloride → HCID 90013739, compound

Participants

Reaction Steps

n-BuLi (1.6 M, 42 mL, 67 mmol) was added slowly to a solution of 2-tetradecyl-thiophene (17.0 g, 237 mmol) in THF (150 mL) at −78° C. and stirred for 30 min. Trimethyltin chloride (13.3 g, 67 mmol) in THF (30 mL) was added dropwise to the resultant suspension and then gradually warmed to room temperature. The reaction mixture was stirred for 18 h and quenched with saturated ammonium chloride solution (100 mL). The mixture was extracted with diethyl ether (2×100 mL) and the combined organic extracts were washed with brine (100 mL). The organic phase was dried and concentrated to give brown oil (26.8 g, 99%), which was used directly in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.02 (d, 1H, J=3.2 Hz), 6.90 (d, 1H, J=3.2 Hz), 2.85 (t, 2H, J=8 Hz), 1.68 (q, 2H, J=7.6 Hz), 1.50-1.20 (m, 22H), 0.88 (t, 3H, J=6.8 Hz), 0.344 (s, 9H).

Provenance & Evidence