Tributyltin Chloride → HCID 9974875, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-trimethylsilylallylamine (21.0 mL, 125. mmol) in diethyl ether (323 mL) at 0° C. under an atmosphere of nitrogen was added 2.5M n-butyllithium in hexanes (100. mL, 250. mmol). The solution was stirred at 0° C. for 15 minutes then the reaction was allowed to warm to room temperature and stirred for 16 hours. To the reaction mixture was added a solution of tributyltin chloride (33.6 mL, 124. mmol) in diethyl ether (158 mL) slowly at 0° C., then the reaction was allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was quenched with saturated ammonium chloride solution then extracted twice with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was purified using column chromatography on silica gel (400 gr Analogix column, gradient DCM to 10% MeOH in DCM over 30 minutes) to give the product (30.6 g, 71%). 1H NMR (400 MHz, CDCl3) δ: 6.81-6.37 (m, 1H), 6.03-5.76 (m, 1H), 3.31-3.17 (m, 2H), 1.60-1.22 (m, 12H), 1.00-0.79 (m, 15H).

Provenance & Evidence