Ethyl Acetoacetate → HCID 67360478, compound

Participants

Reaction Steps

Under a nitrogen atmosphere, to a solution of ethyl acetoacetate (1.0 g, 7.7 mmol) in ethanol (30 mL), 20% sodium ethoxide/ethanol solution (3.1 mL, 7.7 mmol) was gradually added under ice-cooling, and the mixture was stirred at room temperature for 30 minutes. Thereafter, under ice-cooling, a solution of the above (4S)-4-(benzyloxy)-1-bromopentan-2-one (2.1 g, 7.7 mmol) in ethanol (6.0 mL) was gradually added, and the mixture was stirred at room temperature for 3 hours. After the reaction, ethanol was distilled off under reduced pressure and 1N hydrochloric acid (0.20 L) was added to acidify it. After it was extracted with ethyl acetate and successively washed with water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, it was dried with sodium sulfate and the solvent was distilled off under reduced pressure. It was purified by silica gel column chromatography (ethyl acetate/hexane, 1:3, v/v) to give the title compound (1.6 g, 65%) as an oil.

Provenance & Evidence