Dimethyl Sulfoxide → 2-Methoxy-6-methylpyridine-4-carbaldehyde

Temperature

-78 °C

To 50 ml of dichloromethane containing 1.67 ml of oxalyl chloride there was added dropwise 1.36 ml of DMSO at −78° C. under a nitrogen atmosphere, and the mixture was stirred at −78° C. for 30 minutes. Next, 10 ml of a dichloromethane solution containing (2-methoxy-6-methyl-pyridin-4-yl)methanol was added dropwise, and the mixture was stirred at −78° C. for 30 minutes. After then adding 6.7 ml of triethylamine to the reaction mixture over a period of 10 minutes, the mixture was stirred for 30 minutes while raising the temperature from −78° C. to room temperature. Water was added to the reaction mixture, and extraction was performed with dichloromethane. The organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (1.9 g) as a light yellow oil.

1. additionwas added dropwise
2. stirringthe mixture was stirred at −78° C. for 30 minutes
3. stirringthe mixture was stirred for 30 minutes
4. temperaturewhile raising the temperature from −78° C. to room temperature
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationThe desiccating agent was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

ORD record

ord-c28dd32610884feaa418f407a7ef699a

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163787B2