反应详情

To a solution of 2-(4-bromophenyl)-4,4-dimethyl-2-oxazoline (1 g) in dry tetrahydrofuran (10 ml) are added dropwise magnesium (526 mg) and dry tetrahydrofuran (50 ml) under refluxing. The heating of the mixture is stopped, and thereto is added 2-(4-bromphenyl)-4,4-dimethyl-2-oxazoline (4 g) at a slowly refluxing rate, during which the mixture is stirred for 30 minutes, and then thereto is added o-tolualdehyde (2.16 ml) under ice-cooling. The mixture is stirred under ice-cooling for one hour, and stirred at room temperature for two hours, and the reaction is quenched with adding thereto a saturated aqueous ammonium chloride solution. The mixture is extracted with ethyl acetate, and the organic layer is washed successively with 1N hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4˜2:1) to give 2-{4-[1-(2-methylphenyl)-1-hydroxymethyl]phenyl}-4,4-dimethyl-2-oxazoline (3.07 g) as white powder.

1. temperatureunder refluxing
2. temperatureThe heating of the mixture
3. temperaturea slowly refluxing rate
4. temperaturecooling
5. stirringThe mixture is stirred under ice-
6. temperaturecooling for one hour
7. stirringstirred at room temperature for two hours
8. customthe reaction is quenched
9. additionwith adding
10. extractionThe mixture is extracted with ethyl acetate
11. washthe organic layer is washed successively with 1N hydrochloric acid
12. dry with materiala saturated aqueous sodium hydrogen carbonate solution and a saturated sodium chloride solution, dried over magnesium sulfate
13. concentrationconcentrated
14. customThe residue is purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate=4˜2:1)