反应详情

温度

40 °C

Methyl 3-oxo-4-methyl-5-benzyloxypentanoate (1.11 g; 4.43 mmole) was dissolved in dry methanol (5 ml), allylamine (1.26 g) and molecular sieve 3A (0.6 g) were added thereto and then a solution of acetyl chloride (1.04 g; 13.3 mmole) in dry methanol (2 ml) was added thereto with icecooling, followed by stirring at 40° C. for 12 hours. The molecular sieve was removed by filtration, and the filtrate was diluted with ethyl acetate. The reaction mixture was washed successively with a saturated sodium bicarbonate solution and an aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in toluene (5 ml), and gaseous ketene was introduced therein at room temperature. After completion of the reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give methyl 2-acetyl-3-allylamino-4-methyl-5-benzyloxy-2-pentenoate.

1. customThe molecular sieve was removed by filtration
2. additionthe filtrate was diluted with ethyl acetate
3. washThe reaction mixture was washed successively with a saturated sodium bicarbonate solution
4. dry with materialan aqueous sodium chloride solution, dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in toluene (5 ml)
7. additiongaseous ketene was introduced
8. customat room temperature
9. customAfter completion of the reaction
10. customthe solvent was removed under reduced pressure
11. customthe residue was purified by silica gel column chromatography