Water → 780801-56-1

At −78° C., under N2, BuLi (2.5 M in hexanes, 0.80 mL, 2.0 mmol) was added to a solution of TMEDA (0.30 mL, 2.0 mmol) in dry Et2O (20 mL). After addition the mixture was warmed to room temperature. After stirred at room temperature for 30 min the mixture was cooled to −78° C., and added to a solution of 3-chloro-5-methyl-pyridine (0.255 g, 2.00 mmol) (Bushby et al. J. Chem. Soc. Perkin Trans. I 1978, 1578) in dry Et2O (10 mL) pre-cooled at −78° C. The mixture was stirred at −78° C. for 30 min and then warmed to room temperature for 1 h. Water (15 mL) was added, and the mixture was extracted with Et2O (3×40 mL). The organic extracts were combined and dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (CH2Cl2) to afford 3-chloro-5-methyl-pyridine-2-carbaldehyde (0.096 g, 31%). 1H NMR (CDCl3) δ 2.44 (s, 3H), 7.65 (s, 1H), 8.54 (s, 1H), 10.28 (s, 1H).

1. additionAfter addition the mixture
2. temperaturewas cooled to −78° C.
3. temperaturepre-cooled at −78° C
4. stirringThe mixture was stirred at −78° C. for 30 min
5. temperaturewarmed to room temperature for 1 h
6. extractionthe mixture was extracted with Et2O (3×40 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationAfter filtration the solvent
9. customwas removed by evaporation under vacuum
10. customthe residue was purified by flash chromatography on a silica gel column (CH2Cl2)

ORD record

ord-d4ec9c4a142d499c97e971064c6654ab

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07863293B2