Diethyl Malonate → HCID 178470508, compound

Participants

Reaction Steps

Sodium metal (3.8 g, 164 mmol) was added to absolute ethanol (200 mL). The mixture was stirred under reflux until a clear solution was obtained. Diethyl malonate (26.3 g, 164 mmol) was added to this solution which was again heated to reflux, and a solution of 1-(azidomethyl)-4-methoxybenzene (i.e. the product of Step A, 25.5 g, 156 mmol) in ethanol (50 mL) was added at once. The reaction mixture was stirred at reflux for 24 h then the reaction mixture was concentrated to dryness under reduced pressure. The residue was diluted with water (100 mL) and acidified to pH 2 with 1 M aqueous hydrochloric acid, stirred for 30 min, and the solid was filtered off and washed with water. The solid was dried over phosphorus pentoxide. The solid was stirred in chloroform (500 mL) and the insoluble solids were filtered off. Hexanes (400 mL) were added to precipitate the product, which was removed by filtration and dried to afford the title compound (12.0 g) as a beige solid.

Provenance & Evidence