反应详情

A solution of t-butyl lithium (9.0 cm3 of a 2.0M solution in n-pentane) was added at -70° to a stirred solution of 4-bromoanisole (1.13 cm3) in tetrahydrofuran (THF) (20 cm3) under nitrogen. After 10 minutes a solution of anhydrous zinc chloride (1.23 g) in THF (10 cm3) was added and the mixture was allowed to warm to room temperature over 0.5 hour. A mixture of 6-iodo-2-(1H)-quinolone (0.813 g) and tetrakis(triphenylphosphine) palladium (0) (0.03 g) was added and the mixture was heated under reflux for 2 hours. Volatile material was then removed in vacuo and the residue was partitioned between chloroform:methanol, 9:1 (100 cm3) and a solution of ethylenediaminetetraacetic acid disodium salt (7 g) in water (100 cm3). The aqueous phase was further extracted with chloroform:methanol, 9:1 (3×100 cm3), and the combined and dried (MgSO4) organic extracts were evaporated to give an oily solid which was triturated with ethyl acetate. Recrystallization of the residue from ethyl acetate-methanol-chloroform afforded the title compound, m.p. 262°-264° (0.359 g).

1. additionwas added
2. temperaturethe mixture was heated
3. temperatureunder reflux for 2 hours
4. customVolatile material was then removed in vacuo
5. customthe residue was partitioned between chloroform
6. extractionThe aqueous phase was further extracted with chloroform
7. dry with materialdried (MgSO4) organic extracts
8. customwere evaporated
9. customto give an oily solid which
10. customwas triturated with ethyl acetate
11. customRecrystallization of the residue from ethyl acetate-methanol-chloroform