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  • Diisobutylaluminum hydride reductions revitalized: a fast, robust, and selective continuous flow system for aldehyde synthesis.

Diisobutylaluminum hydride reductions revitalized: a fast, robust, and selective continuous flow system for aldehyde synthesis.

Organic letters (2011-12-31)
Damien Webb, Timothy F Jamison
ABSTRACT

A continuous flow system for the multiparameter (flow rate, temperature, residence time, stoichiometry) optimization of the DIBALH reduction of esters to aldehydes is described. Incorporating an in-line quench (MeOH), these transformations are generally complete in fewer than 60 s. Mixing of the DIBALH and ester solutions was observed to be an exceptionally critical parameter for optimum results. This system thus provides general guidelines based on the structure of the ester for selective reduction of an ester without overreduction.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in THF
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in toluene
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in heptane
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in cyclohexane
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in methylene chloride
Sigma-Aldrich
Diisobutylaluminum hydride solution, 1.0 M in hexanes
Sigma-Aldrich
Diisobutylaluminum hydride, reagent grade
Sigma-Aldrich
Diisobutylaluminum hydride solution, 25 wt. % in toluene