1-Methylimidazole → 1-Methyl-5-(tri-n-butylstannyl)imidazole

To a dehydrated tetrahydrofuran solution (10 mL) of 1-methylimidazole (1.6 mL, 18.8 mmol), there was added dropwise a mixture of n-BuLi (18 mL, 45 mmol) and TMEDA (6.7 mL, 44.6 mmol) at −20° C. under nitrogen atmosphere. After stirring for 30 minutes, the mixture was raised to room temperature and stirred for another hour. After again cooling to −20° C., a solution of n-Bu3SnCl (12.5 mL, 46.4 mmol) in tetrahydrofuran (10 mL) was added dropwise thereto, the mixture was raised to room temperature and stirred for 17 hours. The reaction was terminated with water (15 mL), and then extraction was performed twice with ethyl acetate (20 mL). The mixture was then purified by silica gel chromatography (ethyl acetate:methanol=96:4) to yield the title compound (2.2 g, 32%).

1. stirringstirred for another hour
2. temperatureAfter again cooling to −20° C.
3. temperaturethe mixture was raised to room temperature
4. stirringstirred for 17 hours
5. customThe reaction was terminated with water (15 mL)
6. extractionextraction
7. customThe mixture was then purified by silica gel chromatography (ethyl acetate:methanol=96:4)

ORD record

ord-90feac210c1c44c582b949e6c020fb79

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569378B2