Dimethyl Sulfoxide → HCID 18463625, compound

Participants

Reaction Conditions

Reaction Steps

A solution of dimethylsulphoxide (30 mmol, 2.13 ml) in methylene chloride (90 ml) was cooled to −65° C. Trifluoroacetic acid anhydride (20 mmol, 2.82 ml) was added over 3 minutes, then stirred 10 minutes. 2-Hydroxy-1-[4-(methylthio)phenyl]-2-(3-pyridyl)-ethanone (step 2) (10 mmol, 2.59 g) was suspended in ca 10 ml of methylene chloride and rinsed into the reaction vessel using ca 5 ml additional solvent. After 40 minutes, triethylamine (58 mmol, 8.07 ml) was added. The mixture was warmed to 0° C. over 30 minutes, with continued stirring, then-diluted with water (100 ml) and extracted with ethyl acetate (200, then 2×50 ml). The combined organic layers were dried over magnesium sulfate, filtered, concentrated, and subjected to chromatography (2:1 hexane:ethyl acetate), affording the title compound as a yellow solid (2.43 g, 94%), which was used in the next step.

Provenance & Evidence