Our investigation began with a screen of typical conditions used to couple acids with racemic epichlorohydrin (Table ). Equivalents of starting material, preformation of the carboxylate, solvent, temperature and time were explored. In our hands, introducing an excess of epichlorohydrin was advantageous (Entries 4-6). Furthermore, removal of exogeneous solvent led to the best results, giving glycidyl ester 3 in greater than 95% assay yield (AY). While a high stoichiometry of epichlorohydrin was employed, we were encouraged that these conditions could be rendered economical if excess starting material were to be recovered. We subsequently shifted our focus on isolation of the desired compound from the reaction mixture, and the reaction scale was increased to 20 g of pivalic acid and 182 g (10 Eq.) of (S)-epichlorohydrin (Scheme 1). We expected that the high assay yield and simplicity of chemical inputs would facilitate isolation.