Water → HCID 69023608, compound

Participants

Reaction Conditions

Reaction Steps

In a 50-mL one neck round bottom flask, ascorbic acid, Catalog No. A92902 from Aldrich Co. (4.80 g) was dissolved in acetone (16.42 g). In the same flask, cis-endo-5-norbornene-2,3-dicarboxylic anhydride, Catalog No. 247634 from Aldrich Co. (4.42 g), and 4-dimethylaminopyridine, Catalog No. 522821 from Aldrich Co. (0.06 g), were added. The flask was heated while stirring in a 60° C. oil bath for 48 hours. Water (15 mL) was added and the flask was heated for another 12 hours. The product was extracted in ethyl acetate (100 mL) and dry with magnesium sulfate. The product, a mixture of bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid and 3-({(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethoxy}carbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid was isolated by removing ethyl acetate by rotary evaporation.

Provenance & Evidence