Dimethyl Sulfoxide → 2-Acetyl-6-methylpyridine

Temperatur

-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 (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 1-(6-Methyl-pyridin-2-yl)-ethanone (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-Eintrag

ord-5928362ea2f2426dbbf9f14fcd235798

Quelldatensatz

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07273936B2