Water → Tert-butyl 2-acetoxyacetoacetate

Reaction equation

[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].Br[CH:7]([C:15]([CH3:17])=[O:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].O>CN(C=O)C>[C:1]([O:4][CH:7]([C:15]([CH3:17])=[O:16])[C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])(=[O:3])[CH3:2]

Participants

Procedure

To a suspension of sodium acetate (30.76 g, 375 mmol) in DMF (250 mL) was added dropwise tert-Butyl 2-bromo-acetoacetate (59.27 g, 250 mmol). After stirring at ambient temperature for 90 minutes, water (415 mL) was added, followed by extraction with ethyl acetate (3×325 mL). The combined organic layers were washed with water (3×325 mL) and brine (325 mL), dried over Na2SO4 and after filtration, the solvent was removed in vacuo. The resulting oil was purified by distillation (12 mbar, 128°)