反应详情

18.2 g (0.05 mol ) of 6-decyloxy-2-bromonaphthalene (VI-60), 15.4 g (0.1 mol ) of (+)-2-pentynyloxy-3-butyne (VII*-60), 0.5 g of copper iodide, 0.8 g of triphenylphosphine, 0.4 g of bis(triphenylphosphine)-palladium chloride and 100 ml of triethylamine were stirred under reflux for 7 hours in an atmosphere of nitrogen gas. After completion of the reaction, the reaction mixture was poured into ice-aqueous hydrochloric acid and extracted with 200 ml of ethyl acetate. The organic layer was further washed with water and concentrated under reduced pressure. The residue was purified by silica gel chromatography using toluene-ethyl acetate as eluent to obtain 17.9 g (yield 82%) of optically active (+)-6-decyloxy-2-(3-pentynyloxy-1-butynyl)naphthalene (I'-60), [α]D20 =+93 (c=1, chloroform).

1. temperatureunder reflux for 7 hours in an atmosphere of nitrogen gas
2. customAfter completion of the reaction
3. additionthe reaction mixture was poured into ice-aqueous hydrochloric acid
4. extractionextracted with 200 ml of ethyl acetate
5. washThe organic layer was further washed with water
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography