Tributyltin Chloride → HCID 9974875, compound

Temperature

0 °C

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).

1. temperatureto warm to room temperature
2. stirringstirred for 16 hours
3. temperatureto warm to room temperature
4. stirringstirred for 16 hours
5. customThe reaction mixture was quenched with saturated ammonium chloride solution
6. extractionthen extracted twice with diethyl ether
7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
8. concentrationconcentrated
9. customThe residue was purified
10. customon silica gel (400 gr Analogix column, gradient DCM to 10% MeOH in DCM over 30 minutes)

ORD record

ord-21863900dcf0433a9124c3967109db4c

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765746B2