Hydrochloric Acid → HCID 59714895, compound

Participants

Reaction Steps

To an ice-cooled solution of ethyl cyclooctylideneacetate (4.82 g) in tetrahydrofuran (25 mL) was added 1M diisobutylaluminum hydride/hexane (73.8 mL) dropwise over 15 minutes. After stirring the reaction solution under ice cooling for 30 minutes, 2N hydrochloric acid (50 mL) was added. After allowing the solution for its temperature rise to room temperature, it was stirred for additional 30 minutes. The reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and dried over under reduced pressure. To the resulting residue were added pyridine (22 mL), acetic anhydride (10.1 mL) and N,N-dimethylaminopyridine (0.26 g) sucessively. The solution was stirred at room temperature for 18 hours. The reaction solution was diluted with ethyl acetate, washed in turn with 2N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, hexane-ethyl acetate (97:3)] to give the title compound (3.41 g).

Provenance & Evidence