Triethylamine → Bicyclo(2.2.1)hept-5-ene-2-methanol

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Reaction Steps

(exo-rich) 5-norbornene-2-methanol (15 g, 0.121 mol) that was synthesized in (2) of Example 1, triethylamine (Aldrich, 61.2 g, 0.605 mol), and 20 ml of THF were put into the two-neck flask having the volume of 250 ml, and then agitated in the ice-water bath at 0° C. Cinnamoyl chloride (22.1 g, 0.133 mol) was dissolved in 60 ml of THF and then slowly added to the above reactant by using the additional flask. After 10 min, the reactant was heated to normal temperature and the agitation was additionally performed for 1 hour. The solution was diluted with ethyl acetate, moved to the separatory funnel, washed by using water and NaHCO3 several times, and subjected to the distillation under reduced pressure to remove the solvent. The purification was performed by using the column chromatography (hexane:ethyl acetate=20:1) to obtain the product (yield: 88%). The molar ratio (mol %) of the exo isomer and the endo isomer of the product was 58:42.

Provenance & Evidence