反应详情

温度

60 °C

F3, Scheme F. In a 500 mL round bottom flask was placed 250 mL of ethanol from an unopened bottle which is purged with dry nitrogen for ten minutes. 3,4-Diethylpyrrole F2 (1.29 g, 0.01 mol) and 2-acetoxymethyl-5-benzyloxycarbonyl-4-methyl-3 -methoxycarbonylethylpyrrole F1 (7.83 g, 0.02 mol) were added and the mixture heated until all of the pyrroles dissolved. p-Toluenesulfonic acid (65 mg) was added and the reaction temperature maintained at 60° C. The reaction slowly changed color from a clear yellow to a dark red with the product precipitating out of the solution as the reaction progressed. After ten hours the reaction was cooled to room temperature, the volume reduced to one half on a rotary evaporator, and then placed in the freezer for several hours. The product was collected by filtration, washed with a small amount of cold ethanol to afford 4.61 g of an off-white fine powder (61%): 1H NMR (CDCl3, 250 MHz): δ1.14 (6H, t, CH2CH3), 2.23 (6H, s, pyrrole-CH3), 2.31 (4H, t, CH2CH2CO2CH3), 2.50 (4H, q, CH2CH3), 2.64 (4H, t, CH2CH2CO2CH3), 3.60 (10H, br s, CH3CO2 -- and (pyrrole)2 --CH2), 4.44 (4H, br s, C6H5CH2), 6.99-7.02 (4H, m, aromatic), 7.22-7.26 (6H, m, aromatic), 8.72 (1H, s, NH), 10.88 (2H, br s, NH); 13C NMR (CDCl3, 250 MHz): δ10.97, 16.78, 17.71, 19.40, 22.07, 35.09, 51.46, 65.32, 117.37, 119.34, 122.14, 126.58, 126.79, 127.36, 128.19, 133.55, 136.62, 162.35, 173.49; CI MS (M+H)+ 750; HRMS 749.3676 (calc. for C44H51N3O8 : 749.3676).

1. customIn a 500 mL round bottom flask was placed
2. custom250 mL of ethanol from an unopened bottle which is purged with dry nitrogen for ten minutes
3. dissolutiondissolved
4. customThe reaction slowly changed color from a clear yellow to a dark red with the product
5. customprecipitating out of the solution as the reaction
6. temperatureAfter ten hours the reaction was cooled to room temperature
7. customthe volume reduced to one half on a rotary evaporator
8. waitplaced in the freezer for several hours
9. filtrationThe product was collected by filtration
10. washwashed with a small amount of cold ethanol