Methanol → HCID 136396477, compound

Participants

Reaction Conditions

Reaction Steps

In an oven-dried flask under argon, 100 mg tetrakis(2-pyridyl)porphyrin (2-PyP) was dissolved in 5 mL allyl bromide, and reaction was heated at 100° C. for 16 hours. The reaction mixture was heated at 100° C. for 8 hours. Two methods were used to monitor the completion of the reaction. First, the shift of the porphyrin Soret band from λmax=412 nm (methanol) to λmax=418 nm (methanol) was monitored. A second method involved partition of an aliquot of the reaction mixture between H2O and CHCl3 whereby a complete reaction showed no color in the CHCl3 layer. Upon completion of the reaction, the allyl bromide was distilled off under high vacuum, and the residue was triturated with ethyl ether (Et2O). Chromatography was performed on Sephadex LH-20 (column dimensions were 2×20 cm) using methanol as the eluent and fractions that showed porphyrin with λmax=418 nm were retained. Compound VIII was produced as a shiny purple solid, in 78% yield. Absorbance data included the following: UV-vis: λmax (nm) (log10εo) 418(5.29) 512 (4.50) 587(4.32). Electrospray mass spectrometry (ES-MS) showed a molecular ion at 782 (M−4 Br).

Provenance & Evidence