Water → 2-(1-Methyl4-pentenyl)pyridine

Temperature

-20 °C

A solution of 8.46 ml (0.074 mol) of 2-ethylpyridine in 35 ml of tetrahydrofuran was cooled to −20° C. and 47 ml of n-butyllithium (15 w.-% in hexane, 0.074 mol) were subsequently added while stirring. The mixture was allowed to come to room temperature, stirred for another one hour and subsequently cooled back down to −20° C. A solution of 7.52 ml (0.074 mol) of 4-bromo-1-butene in 10 ml of tetrahydrofuran was then added at such a rate that the temperature remained at −20° C. The mixture was allowed to warm to room temperature, stirred for a further 14 hours and hydrolyzed with 50 ml of water. The organic phase was separated off and the aqueous phase was extracted three times with 30 ml each time of diethyl ether. The organic phases were combined, dried over magnesium sulfate, the magnesium sulfate was filtered off and the solvent was distilled off. The residue obtained in this way was distilled at 98-100° C./14 torr. This gave 8.95 g (75%) of 2-(1-methyl-4-pentenyl)pyridine.

1. customto come to room temperature
2. stirringstirred for another one hour
3. customremained at −20° C
4. temperatureto warm to room temperature
5. customThe organic phase was separated off
6. extractionthe aqueous phase was extracted three times with 30 ml each time of diethyl ether
7. dry with materialdried over magnesium sulfate
8. filtrationthe magnesium sulfate was filtered off
9. distillationthe solvent was distilled off
10. customThe residue obtained in this way
11. distillationwas distilled at 98-100° C./14 torr

ORD record

ord-9ceeed5221ba40898b7967fdaaca4815

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07973114B2