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36.1.2.1.2.1 Variation 1: Using Metal Aluminum Hydrides and Related Systems

DOI: 10.1055/sos-SD-036-00032

Cox, L. R.Science of Synthesis, (20083666.

The high reactivity of lithium aluminum hydride makes this an effective reagent for reducing esters to primary alkanols 14.[‌1‌,‌80‌] Reactions are generally carried out in an ethereal solvent and proceed readily at room temperature. The inclusion of silica gel allows reductions to be performed in hydrocarbon solvents (Table 4, entries 1, 2).[‌81‌] The 1-methylpyrrolidin-2-one complex of lithium aluminum hydride also reduces esters readily (entries 3, 4),[‌9‌] as does lithium aluminum hydride in the presence of nickel(II) chloride.[‌82‌] Sodium aluminum hydride exhibits very similar activity to its lithium analogue (entry 5).[‌3‌,‌4‌]

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References


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