Dimethyl Sulfoxide → 2-Acetyl-6-methylpyridine

HRID 917674

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1[N:17]=[C:16]([CH:18]([OH:20])[CH3:19])[CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:12]1[N:17]=[C:16]([C:18](=[O:20])[CH3:19])[CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: -75 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-5928362ea2f2426dbbf9f14fcd235798
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273936B2

Linked notes

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