反应详情

温度

0 °C

4 ml of tetrahydrofuran and 0.62 ml (4.4 mmol) of triethylamine were added to 2.2 ml (4.4 mmol) of isopropylmagnesium chloride (2.0 mol/l tetrahydrofuran solution), the mixture was cooled to 0° C., and a solution having 1.0 g (4.2 mmol) of 3-bromo-5-chloro-2-methoxy-4-methylpyridine dissolved in 5 ml of tetrahydrofuran was dropwise added, followed by stirring for 3 hours to prepare 5-chloro-2-methoxy-4-methyl-3-pyridylmagnesium chloride. A solution having 0.89 g (4.2 mmol) of 2,3,4-trimethoxy-6-methylbenzaldehyde dissolved in 5 ml of tetrahydrofuran was dropwise added to the reaction solution, followed by stirring for 1 hour, and then the temperature was increased to room temperature, followed by stirring further for 1 hour. Water was added to the reaction solution to terminate the reaction, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 1.1 g (yield: 70%) of (2,3,4-trimethoxy-6-methylphenyl)(5-chloro-2-methoxy-4-methyl-3-pyridyl)methanol (pale yellow oily substance).

1. additionwas dropwise added
2. additionwas dropwise added to the reaction solution
3. stirringby stirring for 1 hour
4. temperaturethe temperature was increased to room temperature
5. stirringby stirring further for 1 hour
6. customto terminate
7. customthe reaction
8. extractionfollowed by extraction with ethyl acetate
9. washThe organic layer was washed with a saturated sodium chloride solution
10. dry with materialdried over anhydrous magnesium sulfate
11. filtrationsubjected to filtration
12. distillationthe solvent was distilled off under reduced pressure
13. customThe crude product was purified by silica gel column chromatography