Acetic Acid → 5-Cyclobutylidene-2,2-dimethyl-1,3-dioxane-4,6-dione

Participants

Reaction Conditions

Reaction Steps

Cyclobutanone (0.50 g, 7.1 mmol) (Aldrich, Cat. #C96001) was added to a mixture of ammonium acetate (1.1 g, 14 mmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (1.0 g, 7.1 mmol) (Acros Organics, Cat. #19845) in toluene (10 mL), followed by acetic acid (1.0 mL). The reaction mixture was stirred at 50° C. for 4 h. After cooled to r.t., the mixture was diluted with water, and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%) to afford the desired product (0.68, 48%).

Provenance & Evidence