6-Chloropyridine-3-carbaldehyde → 1-(6-Chloropyridin-3-yl)butan-1-ol

Temperature

-10 °C

To a −10° C. solution of 6-chloronicotinaldehyde (553 mg, 3.91 mmol) in 3.5 mL THF was added n-propylmagnesium bromide (2.34 mL of a 2.0 M solution in THF, 4.69 mmol). The solution was stirred at −10° C. for 10 min, and was then allowed to warm to room temperature. The reaction mixture was quenched by addition of saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate. The organic layer was concentrated. The crude residue was purified by silica gel chromatography to give 1-(6-chloropyridin-3-yl)butan-1-ol (400 mg) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 8.24-8.31 (m, 1H), 7.61-7.67 (m, 1H), 7.25-7.30 (m, 1H), 4.68-4.74 (m, 1H), 2.05-2.26 (br s, 1H), 1.69-1.82 (m, 1H), 1.57-1.68 (m, 1H), 1.19-1.49 (m, 2H), 0.91 (t, J=7.43 Hz, 3H).

1. temperatureto warm to room temperature
2. customThe reaction mixture was quenched by addition of saturated aqueous ammonium chloride
3. extractionThe mixture was extracted with ethyl acetate
4. concentrationThe organic layer was concentrated
5. customThe crude residue was purified by silica gel chromatography

ORD record

ord-bc44083da89f4e8889b2a0396b657711

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073871B2