Sodium hydride → 3-[4-[14-(Trimethylsilyl)tetradecylamino]benzoyl]-2,4-pentanedione

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A solution of 14.2 g. of 2,4-pentanedione and 20 ml. of 1,2-dimethoxyethane is added to a suspension of 6.8 g. of sodium hydride in 110 ml. of 1,2-dimethoxyethane under argon. A solution of 14.0 g. of 4-[14-(trimethylsilyl)tetradecylamino]benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is stirred at room temperature for 12 hours, cooled, poured on ice and extracted with ether. The ether solution is washed with water and saturated sodium chloride solution, dried with anhydrous sodium sulfate and evaporated. The residue is then chromatographed over silica gel to yield the product as a white solid.

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