Dimethylformamide → 3-Formyl-4-methoxypyridine

Temperature

-23 °C

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.

1. stirringstirred for 3 h
2. temperaturecooled to −78° C. again
3. stirringthe solution was stirred at −78° C. for 1 h
4. customThe reaction was quenched at this temperature with brine (150 mL)
5. extractionextracted with ether
6. dry with materialThe combined ether was dried over K2CO3
7. customevaporated in vacuo
8. customThe residue was chromatographed with 50%-80% EtOAc/hexanes

ORD record

ord-b6ccbd0c79d34fd9bc2017651b213737

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601714B2