Tributyltin Chloride → HCID 57516647, compound

Temperature

0 °C

In a round bottomed flask 1-cyclopropylmethyl-4-iodo-1H-imidazole (570 mg, 2.3 mmol) was dissolved in THF (10 mL). The solution was cooled to 0° C. and isopropylmagnesium chloride (2.0 M in THF, 1.15 mL, 2.3 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 1.5 h. Tributylchlorostannane (0.62 mL, 2.3 mmol) was added and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with saturated NH4Cl solution and extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 20% to 50% EtOAc/heptane (containing 0.5% triethylamine) to isolate 740 mg (78%) of 1-cyclopropylmethyl-4-tributylstannanyl-1H-imidazole as a light yellow oil.

1. temperatureThe reaction mixture was warmed to room temperature
2. stirringthe reaction mixture was stirred at room temperature for 1 h
3. customThe reaction mixture was quenched with saturated NH4Cl solution
4. extractionextracted with ethyl acetate (3×)
5. washThe combined organics were washed with brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated
8. customThe residue was purified by silica gel chromatography with 20% to 50% EtOAc/heptane (containing 0.5% triethylamine)

ORD record

ord-076e01a761404fb1b7fdb984cca048ea

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518945B2