反应详情

18.2 g (0.05 mol) of 6-decyloxy-2-bromonaphthalene (VI-59), 10.5 g (0.15 mol) of (+)-3-butyn-2-ol (VII*-59), 0.4 g of copper iodide, 0.7 g of triphenylphosphine, 0.4 g of bis(triphenylphosphine)palladium chloride and 100 ml of diethylamine were stirred under reflux for 12 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 14.3 g (yield 81%) of optically active (+)-6-decyloxy-2-(3-hydroxy-1-butynyl)naphthalene (I'-59), mp 74°-75° C. [α]D20 =+16.9° (c=1, chloroform).

1. temperatureunder reflux for 12 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