6-Chloro-2-methylpyridine-3-carbaldehyde → 1-(6-Chloro-2-methylpyridin-3-yl)ethanol

Temperature

-78 °C

6-Chloro-2-methylnicotinaldehyde (300 mg, 1.93 mmol) was taken up in THF (9.6 ml) under argon and cooled to −78° C. Methylmagnesium bromide (1.29 ml, 3.86 mmol) was added dropwise over 5 minutes. The reaction temperature was maintained at −78° C. for 20 minutes, then was allowed to warm to 0° C. over 2 hours. The reaction was quenched with saturated aqueous ammonium chloride and allowed to warm to room temperature. The reaction mixture was extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude residue was purified by silica gel chromatography (10-75% ethyl acetate/hexanes) to afford the title compound.

1. temperatureThe reaction temperature was maintained at −78° C. for 20 minutes
2. temperatureto warm to 0° C. over 2 hours
3. customThe reaction was quenched with saturated aqueous ammonium chloride
4. temperatureto warm to room temperature
5. extractionThe reaction mixture was extracted three times with ethyl acetate
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe crude residue was purified by silica gel chromatography (10-75% ethyl acetate/hexanes)

ORD record

ord-d867ab50ff424a8fa28ecd75ff12ed02

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2