Ethyl 2-Hydroxybutyrate → ethyl acetoacetate, sodium salt

Participants

Reaction Steps

Jones Reagent (2.67 M, 7.51 mL, 20.05 mmol) was added dropwise to ethyl 2-hydroxybutanoate (2.65 g, 20.05 mmol) in acetone (67 mL) at 0° C., then the reaction mixture was stirred for 10 minutes. Any excess Jones reagent was quenched by the addition of iso-propanol, then the reaction mixture was neutralized with saturated sodium bicarbonate, and the acetone was removed by evaporation. Water was added and the solution was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:4 diethyl ether:hexanes to give 346.7 mg (13%) of ethyl 2-oxobutanoate as an oil. 1H NMR (400 MHz, d6-DMSO): δ 4.19 (q, J=7 Hz, 2H), 2.80 (q, J=7 Hz, 2H), 1.24 (t, J=7 Hz, 3H), 0.94 (t, J=7 Hz, 3H).

Provenance & Evidence