2,2-Dimethyl-1,3-dioxane-4,6-dione → Ethyl 4-(4-fluorophenyl)-3-oxobutanoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-fluorophenylacetyl chloride (4.91 g, 24.3 mmol), 2,2-dimethyl-1,3-dioxane-4,6-dione (3.50 g, 24.3 mmol) and DIEA (5.84 g, 49.8 mmol) in CH2Cl2 (30 mL) was stirred for 1 h at 0° C. and at ambient temp for 2 h. The solution was diluted with CH2Cl2 (40 mL) and the organic phase was washed with 0.1 N HCl and brine, dried over Na2SO4 and evaporated to dryness. The resulting orange solid was suspended in EtOH (100 mL) and refluxed for 2 hours. The solution was evaporated and the resulting orange oil was left in the freezer overnight to give a yellow solid. The crude solid was recrystallized from EtOH to afford ethyl 4-(4-fluorophenyl)-3-oxobutanoate (5.3 g, 86.8% yield).

Provenance & Evidence