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Synlett 2010(7): 1140-1141  
DOI: 10.1055/s-0029-1219578
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Sodium Bis(methoxyethoxy)aluminium Hydride

Akshat Rathi*
Chemistry Research Laboratory, University of Oxford, 12, Mansfield Road, Oxford, OX1 3TA, UK
e-Mail: akshat.rathi@chem.ox.ac.uk;
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Publication History

Publication Date:
23 March 2010 (online)

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Introduction

Sodium bis(methoxyethoxy)aluminium hydride (Red-Al®) is a versatile reducing agent which was developed by Vit and co-workers in 1968. [¹]

Figure 1

Red-Al® exhibits similar reactivity to lithium aluminium hydride but is significantly less sensitive towards air and has higher solubility in aromatic solvents and ethers. In addition, the reactions can be performed at temperatures of up to 200 ˚C. [²] The general mechanism of reduction using Red-Al® involves an initial reaction with an alcohol, formation of hydrogen, and subsequent hydride transfer in an intramolecular fashion. In the absence of such a moiety, the hydride reduction via a mechanism akin to lithium aluminium hydride can be envisaged. The reagent has been used towards the synthesis of many natural products. [³] Some less conventional uses involve the cleavage of benzyl ethers of vicinal methoxy-containing compounds. [4]

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