Diethyl Ether → 3-(3-Buten-1-yl)pyridine

3-(Pyridin-3-yl)propanal (10 g, 74 mmol) is dissolved in THF (200 ml), and thereto is added a solution of trimethylsilylmethyl magnesium chloride in diethyl ether (100 ml, 100 mmol) under ice-cooling, and the mixture is stirred for 15 minutes. The reaction is quenched with a saturated brine (10 ml), and the mixture is extracted with ethyl acetate (300 ml×2), washed with a saturated brine (200 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue are added THF (50 ml) and conc. sulfuric acid (5 ml), and the mixture is heated under reflux for 20 minutes. After being allowed to cool, the reaction solution is neutralized with a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate (200 ml×2). The organic layer is washed with a saturated brine (200 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to give 3-(3-butenyl)pyridine (6.5 g) as a pale yellow oil.

1. temperaturecooling
2. customThe reaction is quenched with a saturated brine (10 ml)
3. extractionthe mixture is extracted with ethyl acetate (300 ml×2)
4. washwashed with a saturated brine (200 ml×2)
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. additionTo the residue are added THF (50 ml) and conc. sulfuric acid (5 ml)
8. temperaturethe mixture is heated
9. temperatureunder reflux for 20 minutes
10. temperatureto cool
11. extractionextracted with ethyl acetate (200 ml×2)
12. washThe organic layer is washed with a saturated brine (200 ml×2)
13. dry with materialdried over anhydrous magnesium sulfate
14. concentrationconcentrated under reduced pressure
15. customThe residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane)

ORD record

ord-2f26274d68cb4537aefd837d8a2c7cab

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555557B1