Dimethyl Sulfoxide → 2-Methoxy-6-methyl-3-nitropyridine-4-carbaldehyde

Temperature

-70 °C

To a −70° C. solution of oxalyl chloride (2.0 mL, 22 =mol) in 50 mL of DCM was added 3.4 mL (44 mmol) of DMSO in 10 mL of DCM by dropping funnel. After 2 min, the reaction mixture was treated with 3.99 g (20 mmol) of the alcohol from step C in 20 mL of DCM. The solution was stirred for an additional 15 min at −70° C., treated with 14 mL (50 mmol) of Et3N and warned to ambient temperature over 90 min. The reaction was quenched with 100 mL of water and the two phases were separated. The aqueous phase was extracted with 100 mL of DCM and the combined organic extracts were washed with 50 mL of brine and dried over MgSO4. The yellow solution was concentrated and chromatographed (2:3 EtOAc/Hexane) to afford the aldehyde as a yellow solid.

1. waitwarned to ambient temperature over 90 min
2. customThe reaction was quenched with 100 mL of water
3. customthe two phases were separated
4. extractionThe aqueous phase was extracted with 100 mL of DCM
5. washthe combined organic extracts were washed with 50 mL of brine
6. dry with materialdried over MgSO4
7. concentrationThe yellow solution was concentrated
8. customchromatographed (2:3 EtOAc/Hexane)

ORD record

ord-efb8b9d216664eb49751428a1fec45fc

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06376499B1