反应详情

A 250-mL three-necked flask equipped with a condenser and charged with propionic acid (60 mL) was heated to reflux. 5-Thiazolecarboxaldehyde (1,373 mg, 3.30 mmol), pyrrole (230 μL, 3.32 mmol), and an additional 5 mL of propionic acid were added. After 3.5 h at reflux, the mixture was cooled to room temperature while exposed to a stream of air. The solvent was removed in vacuo, the residue was redissolved in CHCl3/MeOH/concentrated NH4OH (6:3:1; 100 mL), and the solvent was removed in vacuo. The residue was adsorbed onto silica gel (3 g) and purified by column chromatography (gradient elution. 1–2% MeOH/CH2Cl2) to provide porphyrin 6 (123 mg, 14%) as a solid: 1H NMR (300 MHz, CDCl2) δ −2.70 (s, 2H), 8.67 (s, 4H), 9.02 (s, 8H), 9.38 (s, 4H).

1. customA 250-mL three-necked flask equipped with a condenser
2. temperaturewas heated to reflux
3. temperatureAfter 3.5 h at reflux
4. customThe solvent was removed in vacuo
5. dissolutionthe residue was redissolved in CHCl3/MeOH/concentrated NH4OH (6:3:1; 100 mL)
6. customthe solvent was removed in vacuo
7. custompurified by column chromatography (gradient elution. 1–2% MeOH/CH2Cl2)