反应详情

温度

85 °C

A mixture of 3,4-dihydro-1-(trifluoromethylsulfonyloxy)naphthalene (1.0 g), 3-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl-dihydroxyborane (1.1 g), tetrakis(triphenylphosphine)palladium(0) (0.21 g), lithium chloride (0.46 g), 2M sodium carbonate aqueous solution (5.1 ml) in 1,2-dimethoxyethane (12 ml) was heated at 85° C. and stirred vigorously for 3 hours under nitrogen atmosphere. After being cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between dichloromethane (35 ml) and 2N sodium carbonate aqueous solution (35 ml) and conc. ammonia solution (2.0 ml). The aqueous layer was extracted again with dichloromethane (35 ml) and the combined organic extracts are dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (30:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 2-[3-(3,4-dihydro-1-naphthyl)phenyl]-4,4-dimethyl-4,5-dihydrooxazole (1.05 g).

1. temperatureAfter being cooled to room temperature
2. concentrationthe reaction mixture was concentrated under reduced pressure
3. customThe residue was partitioned between dichloromethane (35 ml) and 2N sodium carbonate aqueous solution (35 ml) and conc. ammonia solution (2.0 ml)
4. extractionThe aqueous layer was extracted again with dichloromethane (35 ml)
5. dry with materialthe combined organic extracts are dried over magnesium sulfate
6. customThe solvent was evaporated in vacuo
7. customthe residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (30:1)
8. additionThe eluted fractions containing the desired product
9. customwere collected
10. customevaporated in vacuo