反应详情

A mechanically stirred solution of magnesium turnings (Mallinckrodt, for Grignard's reaction, 3.75 g., 0.154 mole) and 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (30 g, 0.146 mole) in 50 mL dry tetrahydrofuran under nitrogen was prepared. To this was added a crystal of iodine, 1 mL of dibromoethane and 2 mL of neat p-Iodo n-butylbenzene to initiate the Grignard reaction. After warming to initiate the reaction, the remainder of the p-iodo-n-butylbenzene (40 g, 0.154 mole) in 50 mL dry tetrahydrofuran was added dropwise at a rate sufficient to maintain the reaction at gentle reflux. The addition took 1 hr and the reaction mixture was then heated at reflux for 3 hr. The reaction was then cooled to room temperature and 15 mL water was added dropwise to coagulate the salts. The tetrahydrofuran was decanted and the remaining solids were slurried twice with 200 mL ethyl ether and twice with 300 mL dichloromethane. Each organic extract was decanted from the solids in turn and combined and evaporated under reduced pressure to an oil. The oil was redissolved in 300 mL dichloromethane, washed once with 100 ml saturated sodium chloride solution, dried and concentrated under reduced pressure. The resulting residue was distilled under reduced pressure (0.027 Torr, 130°) to yield 2-(4,4-dimethyl-2-oxazolin-2-yl)-4'-n-butylbiphenyl as an oil, yield 25%.

1. customthe Grignard reaction
2. temperatureAfter warming
3. customthe reaction
4. temperatureto maintain
5. customthe reaction at gentle reflux
6. additionThe addition
7. temperaturethe reaction mixture was then heated
8. temperatureat reflux for 3 hr
9. customThe tetrahydrofuran was decanted
10. extractionEach organic extract
11. customwas decanted from the solids in turn
12. customevaporated under reduced pressure to an oil
13. dissolutionThe oil was redissolved in 300 mL dichloromethane
14. washwashed once with 100 ml saturated sodium chloride solution
15. customdried
16. concentrationconcentrated under reduced pressure
17. distillationThe resulting residue was distilled under reduced pressure (0.027 Torr, 130°)