Fluorenone → 2-(9H-Fluoren-9-ylidene)acetonitrile

Participants

Reaction Steps

528 mg of NaH (in a 55-65% suspension in oil; 13.2 mmol, 2.2 eq) in suspension in 20 mL of DME were introduced into a 100 mL Woulff bottle equipped with a straight condenser. 1.94 mL of diethyl cyanomethylphosphonate (12 mmol, 2 eq) in solution in 5 mL of DME were then added dropwise. After the release of gas, the reaction medium was heated under reflux for 15 min, then 1.08 g of fluoren-9-one (6 mmol, 1 eq) in solution in 5 mL of DME were added dropwise. After refluxing for 2 hours, the reaction was stopped by addition of 40 mL of an aqueous ammonium chloride solution. The medium was taken up with ethyl acetate, and the aqueous phase was extracted with ethyl acetate. The organic phases were collected, dried over MgSO4, filtered and concentrated. The fluoren-9-ylidene-acetonitrile was purified by chromatography over silica gel (CH2Cl2/heptane elution gradient: 80/20).

Provenance & Evidence