反应详情

温度

80 °C

3-(5-Ammoniopentanoyl)pyridinium chloride (103 mg, 0.41 mmol) and 5-(2,4-dichlorophenyl)furfural (128 mg, 0.53 mmol) were combined in a reaction vessel and treated with isopropanol (6 mL). The reaction vessel was sealed and the reaction was heated to 80° C. with stirring overnight. The reaction was then cooled to room temperature, concentrated under reduced pressure and treated with saturated NaHCO3(aq). This mixture was then extracted three times with EtOAc. The EtOAc extracts were washed with brine, combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The recovered material was eluted through a 20 gram column of silica gel with 10.5:7:7:0.5:0.05 (700 mL) and with 7:7:7:1:0.1 (440 mL) hexane:MtBE:CH2Cl2:MeOH:NH4OH (step gradient). One sample was recovered that slowly solidified. This solid material was re-crystallized from a mixture of hot isopropanol and hexane. The crystals were recovered by vacuum filtration, washed with 20% isopropanol in hexane and then with ether, then dried under vacuum giving 71 mg (45%) of a yellow crystalline solid. LC-MS: RT=6.17 min, [M+H]+=383.0.

1. customThe reaction vessel was sealed
2. temperatureThe reaction was then cooled to room temperature
3. concentrationconcentrated under reduced pressure
4. additiontreated with saturated NaHCO3(aq)
5. extractionThis mixture was then extracted three times with EtOAc
6. washThe EtOAc extracts were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. washThe recovered material was eluted through a 20 gram column of silica gel with 10.5:7:7:0.5:0.05 (700 mL) and with 7:7:7:1:0.1 (440 mL) hexane
11. customOne sample was recovered that slowly solidified
12. customThis solid material was re-crystallized from a mixture of hot isopropanol and hexane
13. filtrationThe crystals were recovered by vacuum filtration
14. washwashed with 20% isopropanol in hexane
15. dry with materialwith ether, then dried under vacuum