Hydrogen Peroxide → 3-(2-Hydroxyethyl)-1-{4-nitro-2-[(1E)-prop-1-en-1-yl]phenyl}pyridin-2(1H)-one

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Reaction Conditions

Reaction Steps

452 g (1.60 mmol) of the compound from Example 45A are dissolved in 1.7 ml of anhydrous tetrahydrofuran and cooled to 0° C. 488 mg (176 mmol) of 9-bora-bicyclo[3.3.1]nonane (0.5 M solution in tetrahydrofuran) are added slowly, and the mixture is stirred at room temperature for 2 h. The mixture is then again cooled to 0° C., and 8 ml of 1N aqueous sodium hydroxide solution are added slowly. After the addition has ended, 1.6 ml of 30% strength hydrogen peroxide solution are added dropwise at this temperature. The mixture is stirred at 0° C. for 30 min and then washed with 1.3 ml of 40% strength sodium bisulphite solution to destroy the peroxides and diluted with 500 ml of ethyl acetate. The organic phase is removed and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and, after filtration, concentrated to dryness under reduced pressure. The product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate=2:1). This gives 514 mg (100% of theory) of the desired product.

Provenance & Evidence