Sodium Thiosulfate → 5-(Trifluoromethyl)pyridine-2-carbaldehyde

Dess-Martin periodinane (CAS number 87413-09-0; 13.17 g, 31.10 mmol) was added to a solution of [5-(trifluoromethyl)pyridin-2-yl]methanol (CAS number 31181-84-7; 5.00 g, 28.2 mmol) in DCM (60 ml). The reaction was stirred at room temperature for 18 hours and then a saturated solution of sodium thiosulfate (aq, 100 ml) was added. The reaction was stirred for 45 min at room temperature and then phases separated. The aqueous phase was further extracted with DCM (60 ml) and the combined organics were washed with a saturated solution of sodium bicarbonate (aq, 60 ml), filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-20% ethyl acetate/petrol) to afford the title compound.

1. stirringThe reaction was stirred for 45 min at room temperature
2. customphases separated
3. extractionThe aqueous phase was further extracted with DCM (60 ml)
4. washthe combined organics were washed with a saturated solution of sodium bicarbonate (aq, 60 ml)
5. filtrationfiltered through a hydrophobic frit
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by column chromatography (silica, 0-20% ethyl acetate/petrol)

ORD record

ord-32774602612f44b38157e12d03b4f3db

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156829B2