Dimethylformamide → 3-Fluoro-2-pyridinecarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

Add a solution of n-butyl lithium (34.4 mL, 0.055 mol, 1.6 M in hexanes) to a mixture of 1,4-diazabicyclo-[2.2.2]octane (6.16, 0.055 mol) in diethyl ether (250 mL) at −10 to−20° C. under a nitrogen atmosphere. Stir for 1 h and cool to −70° C. Add 3-fluoropyridine (4.29 mL, 0.05 mol) dropwise and stir for 2.5 hours at this temperature. Add N,N-dimethylformamide (7.75 mL, 0.10 mol) dropwise via syringe and stir for 1 hour near −70° C. Add water (200 mL) when the mixture warms near −20° C. and extract with ethyl acetate. Dry over sodium sulfate and concentrate in vacuo. Elute over silica gel with dichloromethane to give the desired aldehyde (3.06 g, 49%) as a dark solid. MS(ES): (M+1)+ 126.0 m/z.

Provenance & Evidence