Dimethylformamide → 2-Methoxypyridine-3-carbaldehyde

To a stirred solution of 1.7M t-butyl lithium in THF (35.0 mL, 59.6 mmol, 2.60 equiv.) with THF (150 mL) at −78 degrees was added dropwise 2-bromomesitylene (4.56 mL, 29.8 mmol, 1.30 equiv.). After stirring for 1 h, 2-methoxy-pyridine (2.5 g, 22.9 mmol) was added dropwise. This solution was warmed to −23 degrees and stirred for 3 h and then cooled to −78 degrees again. DMF (2.66 mL, 34.4 mmol, 1.5 equiv.) was added, the solution was stirred at −78 degrees 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 on vacuo. The residue was chromatographed with 50%-80% EtOAc/Hexanes to give 2-methoxy-pyridine-3-carbaldehyde (2.34 g, 17.1 mmol, 74.5%) as a yellow solid.

1. temperatureThis solution was warmed to −23 degrees
2. stirringstirred for 3 h
3. temperaturecooled to −78 degrees again
4. stirringthe solution was stirred at −78 degrees for 1 h
5. customThe reaction was quenched at this temperature with brine (150 mL)
6. extractionextracted with ether
7. dry with materialThe combined ether was dried over K2CO3
8. customevaporated on vacuo
9. customThe residue was chromatographed with 50%-80% EtOAc/Hexanes

ORD record

ord-7bf8e3163891401b8f42da50ff57768c

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601714B2