Diethyl Malonate → HCID 69557395, compound

Participants

Reaction Steps

Diethyl malonate (3.1 g, 19.7 mmol, 1.5 equiv) was added dropwise to a solution of sodium (1.25 g, 54.0 mmol, 4.0 equiv) in EtOH (50 mL). 4-Phenyl-cyclohexylmethyl-p-toluene sulfonate (˜13.1 mmol, ˜1.0 equiv, the crude product from the previous step) was added as a solution in 50 mL of EtOH. The resulting mixture was refluxed for 8 h. The reaction mixture was cooled and evaporated to dryness and then dissolved in water (150 mL) and the crude product extracted with 3×100 mL EtOAc. The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography on SiO2 using 10% EtOAc in hexanes to give the desired product as a colorless oil (2.79 g).

Provenance & Evidence