Methyl iodide → 3-(methoxymethyl)pyridine

To a mixture of 10.0 g of 3-hydroxymethylpyridine and 200 ml of THF, 3.7 g of 60% sodium hydride (in oil) was added in small portions at room temperature and then stirred for 15 minutes. To the reaction mixture, 13.0 g of methyl iodide was added dropwise, and the reaction mixture was stirred at room temperature for three hours. To the reaction mixture, 25 ml of water was added. Then, the reaction mixture was concentrated under reduced pressure. To the residue, 25 ml of water was added, followed by extraction with ethyl acetate three times. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 8.17 g of 3-methoxymethylpyridine.

1. additionwas added in small portions at room temperature
2. stirringthe reaction mixture was stirred at room temperature for three hours
3. concentrationThen, the reaction mixture was concentrated under reduced pressure
4. additionTo the residue, 25 ml of water was added
5. extractionfollowed by extraction with ethyl acetate three times
6. washThe combined organic layers were washed with a saturated sodium chloride solution
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-66e83ca908394659a6fb5ca7d53036fb

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609705B2