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Sandra Forbes

Sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al) is comparable to LiAlH₄. The most significant differences lie in the reduction of nitriles, where nitriles are selectively reduced to aldehydes, as well as in the reduction of aromatic aldehydes.

The primary benefits of this reagent, when compared to lithium aluminium hydride, are its insensitivity to oxygen and its excellent solubility in organic solvents. Consequently, a 70% solution in toluene is commercially obtainable.

Recent Literature

γ-Hydroxy-α,β-acetylenic esters serve as precursors for synthesizing γ-hydroxy-α,β-alkenoic esters through trans-selective additions involving either two hydrogen atoms or one hydrogen atom and one iodine atom across the triple bonds. These approaches enable the highly stereoselective preparation of β-substituted and α,β-disubstituted alkenoic esters.
C. T. Meta, K. Koide, Org. Lett., 2004, 6, 1785-1787.

DOI: 10.1021/ol0495366

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Red-Al functions as a highly effective chelation-controlled reducing agent for acyclic acetal-protected R-hydroxy ketones. Typically, it enables the synthesis of 1,2-anti-diols with high diastereomeric ratios and excellent yields.
N. Bajwa, M. P. Jennings, J. Org. Chem., 2008, 73, 3638-3641.

DOI: 10.1021/jo800150x

Quoted from: https://www.organic-chemistry.org/chemicals/reductions/sodiumbis(2-methoxyethoxy)aluminumhydride-red-al.shtm

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