Dimethylformamide → 5-(Dimethoxymethyl)picolinaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of 2.5 M BuLi in hexane (7.6 ml) was added drop-wise, under a N2 atmosphere, to a solution of 2-bromo-5-dimethoxymethyl-pyridine (3.66 g, 15.84 mmol) in THF (60 ml) at −70° C. After 15 minutes, DMF (1.82 ml, 23.5 mmol) was added drop-wise and the mixture was stirred for 30 minutes at −70° C. and then allowed to reach room temperature. The reaction was diluted with H2O and extracted with DCM. The organic phase was dried over Na2SO4 and evaporated to dryness in vacuo. The crude product was purified by flash chromatography (petroleum ether: AcOEt 7:3) to obtain 1.54 g of 5-dimethoxymethyl-pyridine-2-carbaldehyde as a yellow oil.

Provenance & Evidence