Preparation of 1-deuterioaldehydes via tub use of diisobutylaluminum deuteride (DIBAL-D)

Abstract

Deuterioaldehydes, essential precursors In the preparation of chiral primary deuterioalcohols, have been prepared in yields ranging from 55-75% via reduction of methyl and ethyl esters at -78[deg]C with diisobutylaluminun deuterlde (DIBAL-D). The stoichiometry of the DIBAL-D reduction and the time of the reduction were varied depending upon the structure of the reactant. Aliphatic esters were reduced in 6-10 min. at -78[deg]C while aromatic esters were reacted for 1 hr. at -78[deg]C. From 1.0 to 1.S equivalents of DIBAL-D were used to reduce simple monofunctional esters while multifunctional esters required 2.0 to 2.5 equivalents of DIBAL-D.