Triethylamine → HCID 86639970, compound

Participants

Reaction Steps

(exo-rich)5-norbornene-2-methanol (15 g, 0.121 mol) that was synthesized in (2), 4-methoxy cinnamic acid (Aldrich, 21.5 g, 0.121 mol), EDC [1-(3-dimethylaminopropyl)-3-ethylcarboimide hydrochloride] (Aldrich, 37 g, 0.194 mol), and HOBT (1-hydroxybenzotriazol hydrate) (Aldrich, 24.5 g, 0.182 mol) were put into the two-neck flask having the volume of 250 ml and then dissolved in 100 ml of DMF. After the temperature was reduced to 0° C., triethyl amine (Aldrich, 75 ml, 0.605 mol) was slowly dropped. The temperature was increased to normal temperature and maintained for 3 hours. When the reaction was finished, the extraction was performed by using a great amount of ethyl acetate. The resulting substance was washed by using a NaHCO3 aqueous solution, dried by using anhydrous MgSO4, and filtered to remove the solvent by using the rotary evaporator, thereby manufacturing the yellow product oil. The purification was performed by using the column chromatography (hexane:ethylacetate=10:1) to obtain 5-norbornene-2-methyl-(4-methoxy cinnamate) that was the pure product (yield: 80%). The molar ratio (mol %) of the exo isomer and the endo isomer of the product was 58:42.

Provenance & Evidence