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Red-Al, Sodium bis(2-methoxyethoxy)aluminumhydride

Sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al) is comparable to LiAlH4. The most important differences are found in the reduction of nitriles, which are selectively reduced to aldehydes, and in the reduction of aromatic aldehydes.

The main advantages of the reagent compared with lithium aluminium hydride are the insensitivity against oxygen and the good solubility in organic solvents. Thus, a 70%-solution in toluol is commercially available.

Recent Literature

γ-Hydroxy-α,β-acetylenic esters are used as precursors for the preparation of γ-hydroxy-α,β-alkenoic esters by means of trans-selective additions of two hydrogen atoms or one hydrogen atom and one iodine atom across the triple bonds. These methods allow the preparation of β-substituted and α,β-disubstituted alkenoic esters in highly stereoselective manners.
C. T. Meta, K. Koide, Org. Lett., 2004, 6, 1785-1787.

Red-Al is an efficient chelation-controlled reducing reagent for acyclic acetal-protected R-hydroxy ketones. Typically, high diastereomeric ratios and yields can be achieved for the synthesis of 1,2-anti-diols.
N. Bajwa, M. P. Jennings, J. Org. Chem., 2008, 73, 3638-3641.