Tributyltin Chloride → 1,4-Dimethyl-5-(tributylstannyl)-1H-1,2,3-triazole

Temperature

-70 °C

A solution of 1,4-dimethyl-1,2,3-triazole (0.56 g, 5.77 mmol) in THF (5 mL) was added dropwise to a solution of BuLi (2.77 ml, 6.92 mmol, 2.5 M in hexane) in 30 mL of THF at −78° C. under N2. The resulting cloudy mixture was stirred at −70° C. for 1 h. Then tributyltinchloride (1.711 ml, 6.34 mmol) was added. The reaction mixture became clear and was stirred at this temperature for 30 min, and gradually warmed to rt. To the reaction mixture was added 10 ml of NH4Cl and 10 ml of water. The reaction mixture was extracted with ether. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated. The residue was purified on FCC (20% EA/Hexane) to give 1.7 g of a clear liquid (73%). LC-MS (ES) m/z=388 (M+H)+, 1H NMR (CDCl3, 400 MHz) δ 4.05 (s, 3H), 2.38 (s, 3H), 1.5-0.9 (m, 27H)

1. stirringwas stirred at this temperature for 30 min
2. temperaturegradually warmed to rt
3. extractionThe reaction mixture was extracted with ether
4. washThe combined organic layers were washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customThe residue was purified on FCC (20% EA/Hexane)

ORD record

ord-c68221d9c7984e85a9ece043d67b2b99

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946278B2