Tributyltin Chloride → HCID 57516647, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence