HCID 20191518, compound → HCID 20191515, compound

Participants

Reaction Steps

4-Carbethoxy-5-pentyl-2-vinyl-2,3-dihydrofuran prepared in accordance with the procedure of Example I was hydrogenated to obtain 4-carbethoxy-2-ethyl-5-pentyl-2,3-dihydrofuran. For the reaction, 13 grams of the 4-carbethoxy-5-pentyl-2-vinyl-2,3-dihydrofuran and 75 mls ethyl acetate were charged to the reactor of a Parr apparatus. The system was thoroughly purged with nitrogen and 0.65 gram of a hydrogenation catalyst (5 percent palladium on carbon) was added under a nitrogen atmosphere. After additional nitrogen purging, shaking was begun and the system was pressurized with hydrogen to 15 psig. The system was repressurized as necesary until no futher hydrogen uptake was noted. The reaction mixture was then filtered through Dicalite® to remove the catalyst. Ethyl acetate was removed under reduced pressure. Gas chromatographic analysis indicated 98 percent yield crude 4-carbethoxy-2-ethyl-5-pentyl-2,3-dihydrofuran. The crude product was fractionated using a spinning-band distillation apparatus to obtain essentially pure 4-carbethoxy-2-ethyl-5-pentyl-2,3-dihydrofuran (B.P. 112°-114° C. Ε 1 mm Hg. nD≅° 1.4636). The structure ##STR11## was confirmed by infrared and nuclear magnetic resonance spectroscopy.

Provenance & Evidence