Ethyl benzoylformate → Ethyl 2-cyclopentyl-2-hydroxy-2-phenylacetate

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Reaction Steps

A solution of cyclopentylmagnesium chloride in diethyl ether was added dropwise to a solution of 23.5 g of ethyl phenylglyoxylate in 200 ml of tetrahydrofuran under cooling with ice, and this mixture was stirred at the same temperature for 30 minutes. After the addition of a saturated aqueous solution of ammonium chloride, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=30/1 to 20/1) to obtain 11 g of ethyl 2-cyclopentyl-2-hydroxy-2-phenylacetate. This was dissolved in 40 ml of methanol, and 20 ml of a 4N aqueous solution of sodium hydroxide was added thereto at room temperature. This mixture was stirred at the same temperature for 2 hours and then at 50° C. for an hour. After the methanol was distilled off under reduced pressure, the aqueous layer was made weakly acidic with 4N hydrochloric acid and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the resulting solid was washed with diethyl ether/hexane (=1/1) to obtain 8.7 g of the title compound.

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