5-(2-ADAMANTYLIDENE)-2,2-DIMETHYL-1,3-DIOXANE-4,6-DIONE synthesis

Yield:51757-47-2 88%

Reaction Conditions:

with pyridine;piperidine for 120 h;Knoevenagel Condensation;

Steps:

Compound IA. 5-(2-Adamantylidene)-2,2-dimethyl-l,3-dioxane-4,6-dione[00118] This material is commercially available from the Aldrich Company. It can also be synthesized using the following procedure: A solution of 2-adamantanone (1.5 g, 10 mmol), Meldrum's acid (1.73 g, 12 mmol), and a catalytic amount of piperidine (5 drops) in anhydrous pyridine (10 mL) was stirred under argon for 5 days. After this time, the solution was poured into ice water (30 mL), and the resulting mixture was stirred at room temperature for 20 min. At the conclusion of this period, the resulting precipitate was collected by filtration and washed with cold water (15 mL). The resulting solid was dried in vacuo to provide compound IA (2.43 g, 88% yield) as a white solid.

References:

WO2008/24892,2008,A2 Location in patent:Page/Page column 69-70