Synthetic Communications p. 3912 - 3923 (2009)
Update date:2022-07-30
Topics:
Sawada, Tadanobu
Ishii, Hiroyuki
Ueda, Toyotoshi
Aoki, Junji
Phenalen-1-one was obtained in considerable yield by reducing 3-hydroxyphenalen-1-one. Most of known preparation methods are not very practical, either because their yields are very poor or because their processes have many steps. This regioselective 1,2-reduction proceeded by the action of NaBH4 and various cations of rare-earth elements and metals. The yields of phenalen-1-one were examined as a function of typical lanthanoids, molar ratios of lanthanoid ions to 3-acetoxy-phenalen-1-one, and differing methods of protecting the hydroxyl group. Lanthanum chloride (LaCl3) gave the greatest yield (45.3%) of phenalen-1-one at molar ratios higher than a third, probably because La3+ ion is a hard acid and coordinates easily to a hard solvent such as methanol. Further, it has the largest ionic radius among all lanthanoid ions. Copyright Taylor & Francis Group, LLC.
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