反应详情

温度

-78 °C

5.2 ml of a solution of 1.6M n-butyllithium in hexane was added dropwise to a solution of 940 mg of 2,4,4-trimethyl-2-oxazoline in 20 ml of tetrahydrofuran with stirring, at -78° C. The resulting mixture was stirred at -78° C. for 1 hour. After this time, 2.00 g of 3-tert-butyldiphenylsilyloxy-1-propanal [prepared as described in Can. J. Chem., 71, 695 (1993)] in 10 ml of tetrahydrofuran was added to the reaction mixture whilst stirring, maintaining the temperature at -78° C. Stirring was continued at -78° C. for 15 minutes, then the reaction mixture was brought to room temperature and stirred for 30 minutes. At the end of this time, the reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate fraction was washed with water, dried over anhydrous sodium sulfate and the solvent removed by evaporation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using a mixture of 50% v/v ethyl acetate and hexane as the eluent, to afford 2.18 g of the title compound as an oil.

1. stirringThe resulting mixture was stirred at -78° C. for 1 hour
2. stirringwhilst stirring
3. temperaturemaintaining the temperature at -78° C
4. stirringStirring
5. customwas brought to room temperature
6. stirringstirred for 30 minutes
7. extractionextracted with ethyl acetate
8. washThe ethyl acetate fraction was washed with water
9. dry with materialdried over anhydrous sodium sulfate
10. customthe solvent removed by evaporation under reduced pressure
11. customThe resulting residue was purified by silica gel column chromatography
12. additiona mixture of 50% v/v ethyl acetate and hexane as the eluent