Triethylamine → 2-(2'-Nitro-4'-methylsulfonylbenzoyl)-4-propargyl-1,3-cyclohexanedione

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Reaction Steps

4Propargyl-1,3-cyclohexanedione (3.75 g, 25 mmol) and 4-methanesulfonyl-2-nitrobenzoyl chloride (6.06 g, 23 mmol) were dissolved in acetonitrile (100 mL) at 0° C. Triethylamine (9.6 mL, 69 mmol) was added. The mixture was then stirred for 3 hours. To the mixture was then added potassium cyanide (5.0 g) and 18-crown-6 ether (0.5 g) in one portion. The mixture was stirred for 3 days. After dilution with ether, the solution was washed with 1N HC1 and extracted with 5% K2CO3. The basic extract was acidified with concentrated HC1 and extracted with diethyl ether. The ether extract was washed with brine, dried over MgSO4, and concentrated under vacuum, yielding 3.9 g of the desired product, an orange solid, m.p. 65-70° C. The structure was confirmed by nuclear magnetic spectroscopy, infrared spectroscopy, and mass spectroscopy.

Provenance & Evidence