反应详情

7H, FIG. 7B. 2,5-Bis[(3-acetoxypropyl-5-formyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole 7G (5.98 g, 0.011 mol) and LiOH (1.76 g, 0.042 mol) were added to 400 mL of 95% methanol, which had been degassed with nitrogen prior to use, and the mixture heated to reflux under a nitrogen atmosphere. The reaction became homogeneous when heated. After heating for 1.25 hours, the reaction was allowed to cool to room temperature. The product precipitated as a tan color solid as the reaction cooled. The volume of the reaction mixture was reduced to 75 mL on a rotary evaporator and the resulting slurry placed in the freezer for several hours. The product was filtered and then purified by forming a slurry with 400 mL of methanol and 50 mL of water and heating close to boiling. The slurry was first cooled to room temperature, reduced to 1/2 volume under reduced pressure, and placed in the freezer for several hours. The product was collected by filtration and vacuum dried to yield 4.96 g of a tan powder (94%): 1H NMR (CD3OD, 300 MHz): δ 0.96 (6 H, t, CH2CH3), 1.49 (4 H, p, CH2CH2CH2OH), 2.25 (6 H, s, pyrrole-CH3), 2.32-2.43 (8 H, m, CH2CH3 and CH2CH2CH2OH), 3.46 (4 H, t, CH2CH2CH2OH), 3.85 (4 H, s, (pyrrole)2 --CH2),9.34 (2 H, s, CHO); CI MS (M+) 480; HEMS (M)+ 481.2942 (calc for C28H39N3O4, 481.2941).

1. customhad been degassed with nitrogen
2. temperaturethe mixture heated
3. temperatureto reflux under a nitrogen atmosphere
4. temperatureheated
5. temperatureAfter heating for 1.25 hours
6. customThe product precipitated as a tan color solid as the reaction
7. temperaturecooled
8. customThe volume of the reaction mixture was reduced to 75 mL on a rotary evaporator
9. waitthe resulting slurry placed in the freezer for several hours
10. filtrationThe product was filtered
11. custompurified
12. customby forming a slurry with 400 mL of methanol and 50 mL of water
13. temperatureheating
14. customclose
15. temperatureThe slurry was first cooled to room temperature
16. waitplaced in the freezer for several hours
17. filtrationThe product was collected by filtration and vacuum
18. customdried