A study has been made of the [4 + 2]-cycloaddition of cyclopentadiene to vinyl acetate. The main parameters of the production of 5-acetoxynorbene-2 (94.6% yield) in the form of a mixture of exo- and endo-isomers (60 and 40% respectively) have been optimized. It has been established that the hydrogenation of synthesized 5-acetoxybornene-2 in the presence of a nickel-chromium catalyst leads to the production of 2-norbornylacetate consisting of 99.0% exo-isomer.