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To a mixture of methyl 4-formylbenzoate (1d) (20 mmol) and pyrrole (40 mmol), Amberlyst 15 (2 g) was added with stirring. The reaction mixture was stirred at room temperature for 1 hr and then was quenched with aqueous NaOH (0.1 N, 20 mL). The reaction mixture was extracted with chloroform and resin was filtered off. The solvent was removed under reduced pressure and the residue was column chromatographed on flash silica gel (230-400 mesh). Elution of column with chloroform/ethyl acetate (9: 1, v/v) gave 5-(4- carbomethoxyphenyl) dipyrromethane (3d), 5,10-bis(4-carbomethoxyphenyl) tripyrrane (4d) and 5,10,15-tris(4-carbomethoxyphenyl)tetrapyrrane (5d) in 16 %, 12 % and 14 % yields, respectively.
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To a mixture of methyl 4-formylbenzoate (1d) (20 mmol) and pyrrole (40 mmol), Amberlyst 15 (2 g) was added with stirring. The reaction mixture was stirred at room temperature for 1 hr and then was quenched with aqueous NaOH (0.1 N, 20 mL). The reaction mixture was extracted with chloroform and resin was filtered off. The solvent was removed under reduced pressure and the residue was column chromatographed on flash silica gel (230-400 mesh). Elution of column with chloroform/ethyl acetate (9: 1, v/v) gave 5-(4- carbomethoxyphenyl) dipyrromethane (3d), 5,10-bis(4-carbomethoxyphenyl) tripyrrane (4d) and 5,10,15-tris(4-carbomethoxyphenyl)tetrapyrrane (5d) in 16 %, 12 % and 14 % yields, respectively.
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