Water → Ethyl 5-butoxy-1,3-oxazole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Butyl N-[ethoxy(oxo)acetyl]glycinate (783 g, 3.38 mol) was dissolved in 8 L of acetonitrile in a 50 L Chemglass reactor with overhead stirrer and P2O5 (415 g, 2.92 mol) was added in large portions, watching for exotherm. The reaction was heated to 60° C. for 1 hour and LCMS showed the reaction done. After cooling, water (8 L) was added at 20° C. and the reaction was transferred to a 50 L flask. Methylene chloride (8 L) was added, the layers split and the aqueous layer was extracted with three 2 L volumes of methylene chloride. The combined organic layers were washed with two 4 L portions of saturated aqueous NaHCO3, then dried with MgSO4 and evaporated to give an oil that was purified on silica eluting with 0-30% EtOAc/heptane to give the product as an oil.

Provenance & Evidence