Butanal → HCID 13926171, compound

Temperature

-78 °C

To a solution of 2-bromopyridine (1.1 g, 6.96 mmol, purchased from Sigma-Aldrich) in diethyl ether (8 mL) at −78° C. under N2 was added butyllithium (3.1 mL×2.5 M) over 10 min. The reaction solution was stirred at −78° C. for 1.0 hr. To the mixture was added butyraldehyde (0.602 g, 8.35 mmol, purchased from Sigma-Aldrich) dropwise over 10 min. After stirring at −78° C. for 15 min, the mixture was allowed to warm to rt and stirred at rt for 1.5 hr. The reaction mixture was poured into saturated aqueous NH4Cl solution (10 mL), diluted with water (15 mL), and extracted with EtOAc (20 mL×3). The organic layers were combined, washed with water, sat. aq. NaCl solution, and dried over MgSO4. After removal of organic solvents under reduced pressure, purification of the residue by flash chromatography on silica gel with 20-80% EtOAc/Hexanes provided the title compound as a white solid. Mass Spectrum (ESI) m/z=152.1 (M+1).

1. stirringAfter stirring at −78° C. for 15 min
2. temperatureto warm to rt
3. stirringstirred at rt for 1.5 hr
4. extractionextracted with EtOAc (20 mL×3)
5. washwashed with water, sat. aq. NaCl solution
6. dry with materialdried over MgSO4
7. customAfter removal of organic solvents
8. customunder reduced pressure, purification of the residue by flash chromatography on silica gel with 20-80% EtOAc/Hexanes

ORD record

ord-7ec440db928c4d94b75eae92033f7d87

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569341B2