Trimethyltin chloride → HCID 59523083, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.16 g (0.298 mmol) of compound 13 in 24 mL of THF was cooled to −78° C. The resulting suspension was treated dropwise with 0.29 mL (0.725 mmol) n-BuLi (2.5 M in hexanes) and stirred for 30 minutes. The dry ice bath was removed and the mixture was stirred at ambient temperature for 30 minutes. The mixture was treated with 0.167 g (0.84 mmol) of trimethyltin chloride and heated in an oil bath at 60° C. for 30 minutes. The mixture was concentrated in vacuo. The resulting oily solid was triturated with 15 mL of hexanes and filtered warm. The filtrate was concentrated in vacuo to a yellow oil that solidified on standing to give 252 mg (98% yield) of compound 14. 1H NMR (500 MHz) δ 4.46 (t, 4H, J=6.5 Hz), 1.88-1.22 (m, 40H), 0.88 (t, 6H, J=7.0 Hz), 0.44 (s, 18H).

Provenance & Evidence