Dimethylformamide → 3-Formyl-4-methoxypyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1.7 M t-butyl lithium in THF (35.0 mL, 59.6 mmol) with THF (150 mL) at −78° C. was added dropwise 2-bromomesitylene (4.6 mL, 29.8 mmol). After stirring for 1 h, 4-methoxy-pyridine (2.5 g, 22.9 mmol) was added dropwise. This solution was warmed to −23° C. and stirred for 3 h and then cooled to −78° C. again. DMF (2.7 mL, 34.4 mmol) was added and the solution was stirred at −78° C. for 1 h. The reaction was quenched at this temperature with brine (150 mL) and extracted with ether. The combined ether was dried over K2CO3 and evaporated in vacuo. The residue was chromatographed with 50%-80% EtOAc/hexanes to give 2.1 g (65%) of 4-methoxy-pyridine-3-carbaldehyde as a yellow solid.

Provenance & Evidence