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-f6514a278ba945848cd749b75f25e7ce

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278465B2