Hydrochloric Acid → 2-Cyclopropylpyridine-3-carbaldehyde

Temperature

0 °C

2-cyclopropyl-3-cyano-pyridine (18.5 g, 128 mmol) was dissolved in toluene (400 ml) and DIBAL (1.01M in toluene, 153 ml) was added thereto at 0° C. After stirred at 0° C. for 1 h, the reaction mixture was poured into 2N HCl aq (90 ml); and 5N NaOH aq. (40 ml) was added thereto. The mixture was extracted with EtOAc and the organic layer was washed with brine, dried over MgSO4. The desiccant was removed through filtration, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to 7/3) to obtain the intended compound as a pale yellow solid.

1. customat 0° C
2. extractionThe mixture was extracted with EtOAc
3. washthe organic layer was washed with brine
4. dry with materialdried over MgSO4
5. customThe desiccant was removed through filtration
6. concentrationthe filtrate was concentrated under reduced pressure
7. customthe resulting residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to 7/3)

ORD record

ord-d84f986a2ad7486bab9d5d274e42a325

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935712B2