Diethyl Malonate → HCID 56957354, compound

Participants

Reaction Steps

Diethyl malonate (4.53 mL, 30.0 mmol) was added gradually at 0° C. to a mixed liquid containing sodium hydride (55 wt % in oil, 2.95 g, 67.5 mmol) and anhydrous dimethylsulfoxide (60 mL). Following stirring of the resulting mixed liquid at this temperature for 30 minutes, 3-bromobenzyl bromide (15.7 g, 63.0 mmol) was added. The resulting mixed liquid was stirred at room temperature for 2 hours, and a saturated aqueous solution of ammonium chloride was then added to halt the reaction. The organic layer was separated from the mixed liquid, and the water layer was extracted with ethyl acetate. The thus obtained organic layer was washed with a saturated saline solution and then dried using anhydrous magnesium sulfate. The organic layer was then filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:1), yielding the title compound (4c) (12.7 g, 25.5 mmol) as a white solid in a yield of 85%.

Provenance & Evidence