Methyl iodide → 2,2-Dimethyl-1H-indene-1,3(2H)-dione

Participants

Reaction Steps

Potassium fluoride on Celite® [loading wt: 50% purchased from Sigma-Aldrich Co.] (5.8 g, ˜50 mmol) is heated at 135° C. for 2 hours under vacuum (<20 torr). The solid is then permitted to cool to room temperature and placed under a nitrogen atmosphere at which time a solution of indan-1,3-dione (CAS#606-23-5, 1.46 g, 10.0 mmol) in acetonitrile (15 mL) is added followed by iodomethane (1.8 mL, 30 mmol). The reaction is heated in a sealed vessel at 70° C. overnight. The reaction mixture is cooled to room temperature and filtered through a pad of Celite®. The eluent is concentrated and the resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:9) to furnish 2,2-dimethyl-indan-1,3-dione 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (s, 6 H), 7.84-7.89 (m, 2 H), 7.96-8.02 (m, 2 H).

Provenance & Evidence