反应详情

1.38 g (5.50 mmol) (E)-4-butyloxy-3-methoxycinnamic acid was suspended in 3 ml acetonitrile. A mixture of 0.84 g (5.50 mmol) 1,8-diazabicyclo[5 4.0]undec-7-ene(1,5-5) (DBU) and 3 ml acetonitrile was added dropwise over a period of 5 minutes. 0.46 g (1.25 mmol) tetrabutylammonium iodide and 0.68 g (5.00 mmol) 6-chlorohexanol was added and the resulting mixture was then refluxed for 6 hours. The reaction mixture was cooled and then extracted using ethyl acetate and water. The ethyl acetate phase was washed with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by chromatography using a silica gel column (120 g) and toluene:ethyl acetate (1:1) as eluant to give 1.39 g (79%) (E)-4-butyloxy-3-methoxycinnamic acid 6-hydroxyhexyl ester as colourless oil.

1. additionwas added dropwise over a period of 5 minutes
2. temperaturethe resulting mixture was then refluxed for 6 hours
3. temperatureThe reaction mixture was cooled
4. extractionextracted
5. washThe ethyl acetate phase was washed with water
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated by rotary evaporation
9. customThe residue was purified by chromatography