반응 #3191

반응 방정식

3,4-Diethylpyrrole

2-acetoxymethyl-5-benzyloxycarbonyl-4-methyl-3-methoxycarbonylethylpyrrole

p-Toluenesulfonic acid

→

powder

수율 61.0%

2,5-Bis[(5-benzyloxycarbonyl-4-methyl-3-methoxycarbonylethylpyrrol-2-yl)methyl]-3,4-diethylpyrrole

수율 61.0%

반응 조건

후처리

1. 1
   기타In a 500 mL round bottom flask was placed
2. 2
   기타250 mL of ethanol from an unopened bottle and this was then purged with dry nitrogen for ten minutes
3. 3
   workup.DISSOLUTIONdissolved
4. 4
   기타The reaction slowly changed color from a clear yellow to a dark red with the product
5. 5
   기타precipitating out of the solution as the reaction
6. 6
   온도After ten hours the reaction was cooled to room temperature
7. 7
   기타the volume reduced to one half on a rotary evaporator
8. 8
   workup.WAITplaced in the freezer for several hours
9. 9
   여과The product was collected by filtration
10. 10
    세척washed with a small amount of cold ethanol

실험 절차

7C, FIG. 7. In a 500 mL round bottom flask was placed 250 mL of ethanol from an unopened bottle and this was then purged with dry nitrogen for ten minutes. 3,4-Diethylpyrrole 7B (1.29 g, 0.01 mol) and 2-acetoxymethyl-5-benzyloxycarbonyl-4-methyl-3-methoxycarbonylethylpyrrole 7A (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, CH2 CH3), 2.23 (6H, s, pyrrole-CH3), 2.31 (4H, t, CH2CH2 CO2CH 3), 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, C6H5 CH2), 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 C44H51 N3O8 : 749.3676).

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