Water → HCID 14418356, compound

Participants

Reaction Conditions

Reaction Steps

Dimethyl malonate (10.00 g, 75.7 mmol) was added to a suspension of NaH (60% in oil, 3.33 g, 83.3 mmol) in THF (100 mL) over 20 minutes at room temperature. The mixture was heated at 80° C. for 15 minutes, then a solution of α-bromotolunitrile (14.84 g, 75.69 mmol) in THF (100 mL) was added. Heating was continued at 80° C. for 1 hour, then at 50° C. for 64 hours. Water (30 mL) was added, and the aqueous phase was extracted with EtOAc (3×20 mL). The combined organic phases were dried (MgSO4) and concentrated. Purification of the crude material on silica gel (25% EtOAc/hexanes) gave the title compound as colourless crystals (8.49 g, 45%).

Provenance & Evidence