2.1.3 Sodium bis(2-Methoxyethoxy)aluminum Hydride (SMEH) [NaAlH2(OCH2CH2OMe)2]
Sodium bis(2-methoxyethoxy)aluminum hydride (SMEAH) is a commercially available reducing agent with trade name Red-Al. It is more selective than LAH and the reduction can be carried out in aromatic hydrocarbons as well as other ethers solvent (Scheme 12).
M. Gugelchuk, Encyclopedia of Reagents for Organic Synthesis, John Wiley and Sons., Inc., L. A. Paquette, Ed., New York, 1995, 7, 4518. |
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Scheme 12 |
Examples:
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S. E. Denmark, T. K. Jones, J. Org. Chem. 1982, 47, 4595. |
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M. Ishizaki, O. Hoshino, Y. Iitaka, J. Org. Chem. 1992, 57, 7285. |
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R. B. Gammill, L. T. Bell, S. A. Mizsak, Tetrahedron Lett. 1990, 31, 5301. |