Dimethyl Sulfoxide → 2-Acetyl-6-methylpyridine

Temperature

-75 °C

To a −75° C. solution of oxalyl chloride (20 mL, 225 mmol, 1.1 equiv) in methylene chloride (300 mL) was slowly added a solution of dimethylsulfoxide (32 mL, 2.2 equiv) in methylene chloride (400 mL) over 1 hour. The resulting solution was stirred at −75° C. for 10 min, and then slowly treated with a solution of 1-(6-methyl-pyridin-2-yl)-ethanol of Step A (28 g, 204 mmol, 1 equiv) in methylene chloride (600 mL). The reaction mixture was stirred for 10 min at the same temperature, and then slowly treated with triethylamine (140 mL, 1.02 mol, 5 equiv). The resulting mixture was warmed to 20° over 2 hours, and then quenched with water (500 mL). The organic phase was separated, dried over magnesium sulfate and concentrated in vacuo to yield the crude material. Silica gel chromatography (3:1 hexanes/ethyl acetate) yielded the title compound (25.36 g, 92%).

1. stirringThe reaction mixture was stirred for 10 min at the same temperature
2. temperatureThe resulting mixture was warmed to 20° over 2 hours
3. customquenched with water (500 mL)
4. customThe organic phase was separated
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customto yield the crude material

ORD record

ord-8dcd4b09df034dbc9ae785a205b740cf

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417041B2