反应详情

温度

0 °C

To a suspension of NaH (448 mg/l 1.2 mmol) in THF (22 ml) was added a solution of methyl acetoacetate (1.30 g/11.2 mmol) in THF (4.5 ml) dropwise at 0° C. over 15 minutes. After 20 minutes at 0° C., n-butyl lithium (7,3 ml/11.2 mmol) was added dropwise at 0° C. over 15 minutes. After 20 minutes at 0° C., a solution of 3-{[2-(bromomethyl)benzyl]oxy}-N-trityl-1-propanamine in THF (6.6 ml) was added dropwise at 0° C., and the solution was stirred at 0° C. for 3 hours. The mixture was quenched with water, and the whole was extracted with ethyl acetate (100 ml×2). The combined organic layer was washed with brine (30 ml), dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in diethylether (100 ml) and hexane (100 ml). The solution was washed with water (50 ml×5), brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography (SiO2, 200-350 mesh/hexane:ethyl acetate=10:0-3:1) to afford a colorless oil (3.70 g/74%).

1. waitAfter 20 minutes at 0° C.
2. customThe mixture was quenched with water
3. extractionthe whole was extracted with ethyl acetate (100 ml×2)
4. washThe combined organic layer was washed with brine (30 ml)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in diethylether (100 ml)
9. washThe solution was washed with water (50 ml×5), brine
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe residue was purified by column chromatography (SiO2, 200-350 mesh/hexane:ethyl acetate=10:0-3:1)
14. customto afford a colorless oil (3.70 g/74%)