Pyridine → 3-[2-Methoxy-3-(methylsulfinyl)-4-(trifluoro-methyl)benzoyloxy]cyclohex-2-en-1-one

Participants

Reaction Conditions

Reaction Steps

3.0 g of 2-methoxy-3-methylsulfinyl-4-trifluoromethylbenzoic acid and 1.68 g of 1,3-cyclohexanedione are suspended in 20 ml of ethyl acetate and 5.61 ml of pyridine under an inert atmosphere and cooled to −25° C. with stirring. 1.73 g of thionyl chloride are then slowly added dropwise such that the temperature always remains below −20° C. Following the complete addition of the thionyl chloride, the mixture is stirred for a further 20 minutes. 38 μl of cold water are added, and the mixture is warmed to 0° C. 10 ml of ethyl acetate and a further 10 ml of water are then added. After separating the organic phase from the aqueous phase, the aqueous phase is extracted twice with 5 ml of ethyl acetate in each case. The combined organic phases are dried, giving 3.57 g of 3-[2-methoxy-3-(methylsulfinyl)-4-(trifluoro-methyl)benzoyloxy]cyclohex-2-en-1-one (85.5% yield).

Provenance & Evidence