Diethyl Malonate → Diethyl tetrahydropyran-4,4-dicarboxylate

Participants

Reaction Steps

Sodium (20.7 g, 900 mmol) was carefully dissolved in dry ethanol (300 mL) and to this mixture was added diethyl malonate (144 g, 900 mmol) and 2, bis-(2-chloroethyl)ether (129 g, 900 mmol). The reaction mixture was refluxed for 15 h and cooled to room temperature. The solvent was removed by rotary evaporation, the product acidified with 10% HCl (200 mL), extracted with ethyl acetate (4×200 mL) and dried (Na2SO4). Removal of solvent by rotary evaporation, followed by distillation (170–175° C., 22 mm Hg) furnished the product (98.0 g, 48% yield).

Provenance & Evidence