Methyl formate → 2,4-Dichloropyridine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of diisopropylamine (2.6 mL, 18.5 mmol) in THF (18.5 mL) was stirred at −78° C. as a 2.5 N solution of n-butyl lithium (7.4 mL, 18.5 mmol) was added. The solution was stirred at 0° C. for 30 minutes, then cooled to −78° C. for 30 minutes before the addition of 2,4-dichloropyridine (2 mL, 18.5 mmol). The solution was stirred at −78° C. for another 30 minutes before the addition of methyl formate (1.14 mL, 18.5 mmol). The solution was stirred for 30 minutes then was partitioned between ethyl acetate and saturated aqueous NaHCO3. The organic layer was dried with MgSO4, filtered and concentrated. The residue was purified by chromatography (silica gel, hexane to 3:7 ethyl acetate:hexanes) to provide 2,4-dichloro-3-pyridinecarbaldehyde (2.18 g, 67%). 1H NMR (400 MHz, DMSO-d6): δ 10.29 (s, 1H), 8.54 (d, J=5 Hz, 1H), 7.75 (d, J=5 Hz, 1H).

Provenance & Evidence