Tetrahydrofuran → 5-(2-Methylprop-1-en-1-yl)pyridine-2-carbaldehyde

Temperature

-10 °C

Under a nitrogen atmosphere, 2.0M tetrahydrofuran solution (11.2 mL) of butylmagnesium chloride was diluted with tetrahydrofuran (200 mL). The solution was cooled to −10° C., 1.6M hexane solution (28.1 mL) of n-butyllithium was added dropwise thereto, and the mixture was stirred at −10° C. for 10 min. To the reaction solution was added dropwise a solution (50 mL) of 2-bromo-5-(2-methylprop-1-en-1-yl)pyridine (11.9 g) in tetrahydrofuran, and the mixture was stirred at −10° C. for 30 min. To the reaction solution was added N,N-dimethylformamide (8.65 mL), and the mixture was stirred at −10° C. for 3 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:99-10:90, volume ratio) to give the title compound (7.47 g, yield 83%) as a pale-yellow oil.

1. stirringthe mixture was stirred at −10° C. for 30 min
2. stirringthe mixture was stirred at −10° C. for 3 hr
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed successively with water and saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:99-10:90, volume ratio)

ORD record

ord-9e3197461b344bb19accd9915879d58e

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08349886B2