Potassium Carbonate → p-Ferrocenylphenylacetylene

Participants

Reaction Steps

A solution of 3 (1.5 g, 4.2 mmol) in anhydrous THF/MeOH (2:1, 30 mL) was treated with K2CO3 (1.2 g, 8.4 mmol) and the mixture was stirred at rt for 30 min. The solvent was removed under reduced pressure affording an orange solid. The residue was dissolved in ether (50 mL), washed with H2O (3×50 mL), dried (MgSO4) and filtered. The solvent was removed under reduced pressure. Purification by column chromatography (silica, petroleum ether/ethyl ether, 10:2) afforded an orange solid (1.0 g, 90%): mp 104-106° C.; 1H NMR δ 3.11 (s, 1H), 4.04 (s, 5H), 4.35 (t, J=2.4 Hz, 2H), 4.65 (t, J=2.4 Hz, 2H), 7.42 (s, 4H); 13C NMR δ 66.5, 69.3, 69.7, 84.0, 94.1, 105.5, 120.3, 125.7, 132.1, 140.3; FAB-MS obsd 286.0460, calcd exact mass 286.0445 (C18H14Fe). Physical properties concur with published data (Simionescu et al. (1976) J. Organomet. Chem., 113: 23-28).

Provenance & Evidence