Carbon Tetrachloride → HCID 53997994, compound

Participants

Reaction Steps

To a solution of aromatic compound 179 (5.0 g, 20.16 mmol) in HPLC grade acetonitrile (60 mL), carbon tetrachloride (60 mL), and water (120 mL) was added sodium periodate (86.24 g, 403.32 mmol, 20 equiv.), followed by RuCl3 (414 mg, 10 mol %). The mixture was stirred vigorously overnight at room temperature, and diluted with methylene chloride (400 mL). The mixture was filtered through a pad of Celite to remove the solid precipitate. The organic portion was separated, and the aqueous was further extracted with methylene chloride. After the combined organic portions concentrated, the residue was dissolved in ether and applied to a column of Florisil. The compound was eluted with 3% methanol in ether, evaporated to a paste that was dissolved in methanol (100 mL). Potassium carbonate (8.0 g) was added, and the mixture was refluxed for 6 hours. The solvent was evaporated, and the solid residue was dissolved in water. The pH was adjusted to 2 by the careful addition of concentrated HCl while being cooled in ice water bath and stirred. Chloroform (200 mL) was added to the solution and stirred as such overnight at room temperature. The organic phase was separated, and the aqueous portion was further extracted with chloroform. After drying, the solvent was evaporated to give the lactone 180 5.0 g. NMR (CDCl3) δ 4.36 (app. t, 1H, CHaHbO), 3.85 (app. t, 1H, CHaHbO), 2.46 (m, 2H, CHcHd C═O), 2.13 (m, 2H, CHCH2C═O), 1.60 (m, 1H, CH(Me)2), 1.35 (m, 1H, CH3CHCH(Me)2), 0.86 (d, 3H, CH3) and 0.72 (t, 3H, CH3).

Provenance & Evidence