Diethyl Ether → 1,3-Cyclopentanedione, 2,2-dimethyl-

Participants

Reaction Steps

A solution of potassium hydroxide (15.0 g, 0.27 mol) in water (40 ml) was added to a stirred solution of 2-methylcyclopentane-1,3-dione 1 (25.0 g, 0.22 mol) in 1,4-dioxane (120 ml) at room temperature. Methyl iodide (100 g, 0.70 mol) was then added and the resulting solution was heated under reflux for 15 hours. The mixture was then cooled to room temperature and extracted with ethyl acetate (4×160 ml). The combined extracts were then dried over MgSO4 and evaporated in vacuo. Flash chromatography (SiO2, 60% diethyl ether in hexane) gave the dione 2 (18.0 g, 0.14 mol, 64%) as a white solid; δH (300 MHz, CDCl3) 2.80 (4H, s, CH2CH2), 1.16 (3H, s, CH3), 1.15 (3H, s, CH3); δC (75.5 MHz, CDCl3) 216.3 (s), 52.6 (s), 34.5 (t), 20.2 (q).

Provenance & Evidence