Réaction #3190

Équation de réaction

3,4-Diethylpyrrole

benzyl 5-(acetoxymethyl)-3-methyl-4-ethyl-pyrrole-2-carboxylate

p-toluenesulfonic acid

→

powder

Rendement 82.0%

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

Rendement 82.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   workup.WAITplaced in the freezer for several hours
2. 2
   FiltrationThe product was then collected by filtration
3. 3
   Lavagewashed with a small amount of cold ethanol
4. 4
   Autrerecrystallized from dichloromethane-ethanol

Mode opératoire

3,4-Diethylpyrrole (2A, FIG. 2)28 (0.6, 4.9 mmol), benzyl 5-(acetoxymethyl)-3-methyl-4-ethyl-pyrrole-2-carboxylate (2B, FIG. 2)29 (2.5 g, 7.9 mmol), and p-toluenesulfonic acid (0.15 g) were dissolved in 60 mL of absolute ethanol and heated at 60° C. for 8 h under nitrogen. The resulting suspension was reduced in volume to 30 mL and placed in the freezer for several hours. The product was then collected by filtration, washed with a small amount of cold ethanol, and recrystallized from dichloromethane-ethanol to afford a white powder (2.07 g, 82%): mp 211° C. NMR spectra and high resolution mass spectral data were obtained as described and are reported 13a.

Source