Methyl iodide → HCID 59199412, compound

Participants

Reaction Steps

Potassium fluoride on Celite® [loading wt: 50% purchased from Sigma-Aldrich Co.] (17.4 g, ˜150 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 4-chloro-indan-1,3-dione (CAS#20926-88-9, 5.6 g, 31.0 mmol), which can be prepared as described by Smith, H.; et al. Journal of Medicinal Chemistry, 1973, 16, 1334-1339, in acetonitrile (45 mL) is added. Iodomethane (5.4 mL, 90 mmol) is then added to the mixture. 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 reaction mixture is cooled to room temperature and filtered through a pad of Celite®. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 0:1 to 1:9) to furnish 4-chloro-2,2-dimethyl-indan-1,3-dione; 1H NMR (400 MHz, CDCl3) δ ppm 1.32 (s, 6 H), 7.74-7.82 (m, 2 H), 7.91 (dd, J=7.1, 1.5 Hz, 1 H).

Provenance & Evidence