Methanol → Porphyrinogen

Participants

Reaction Steps

β-Decafluoro-meso-decamethylcalix[5]pyrrole, 46 and β-hexadecafluoro-meso-hexadecamethylcalix[8]pyrrole, 48. To a round bottom flask containing methanol (37.5 mL), difluoropyrrole (773 mg, 7.50 mmol), and acetone (548 μL, 7.50 mmol were added. After dissolution of the reactants, methanesulfonic acid (490 μL, 7.50 mmol) was added and the reaction mixture was allowed to stir at ambient temperature for 2 days. The reaction mixture was then washed with aqueous NaCO3 (200 mL saturated) and taken into dichloromethane (100 mL). The resulting organic layer was then washed with water (2×100 mL), dried (Na2SO4), and the solvent was removed on the rotary evaporator. Purification of the crude reaction mixture, which was found to contain 44, 46 and 48 in appriciable yields as judged by TLC analysis, was effected via flash chromatography, using hexanes-acetone 4/1 v/v as the eluent. This resulted in the isolation of 44 (rf=0.4, 560 mg, 0.98 mmol, 52%), 46 (rf=0.2, 249 mg, 0.35 mmol, 23%), and 48 (rf=0.1, 150 mg, 0.13 mmol, 14%).

Provenance & Evidence