Methanol → 6-Chloropyridine-3-carbaldehyde

Temperature

5 °C

To a cooled (5° C.), stirred solution of 2-chloro-5-cyanopyridine (25.0 g) in anhydrous toluene (540 mL) was added a 1 M solution of diisobutylaluminum hydride (189 mL) over a 30-min period. The resulting red-colored solution was treated with methanol (50 mL) and 2M sulfuric acid (150 mL), sequentially. The resulting biphasic solution was allowed to warm to ambient temperature and stirred for 1 h. The reaction mixture was extracted with ethyl acetate, the combined organic layers were washed with saturated aqueous sodium bicarbonate and saturated aqueous brine. The organic phase was stirred over activated charcoal for 20 min, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 23.5 g of the title compound (I-2a) as a light-yellow colored solid.

1. temperatureto warm to ambient temperature
2. extractionThe reaction mixture was extracted with ethyl acetate
3. washthe combined organic layers were washed with saturated aqueous sodium bicarbonate and saturated aqueous brine
4. stirringThe organic phase was stirred over activated charcoal for 20 min
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-9a90e1bc43a349ab8ef2da19503af270

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06939867B2