Ethyl bromoacetate → Ethyl 4-oxo-3-propanoylhexanoate

Participants

Reaction Steps

To a suspension of sodium hydride (5.2 g, 130 mmol, 60% in mineral oil) in tetrahydrofuran (100 mL) at 0° C. was added dropwise a solution of heptane-3,5-dione (16.6 g, 130 mmol) in tetrahydrofuran (30 mL). After 15 minutes, bromo-acetic acid ethyl ester (14.4 mL, 130 mmol) was added and the reaction mixture was stirred for 16 h at room temperature. The reaction mixture was poured into an aqueous ammonium chloride solution and extracted several times with ethyl acetate. The combined ethyl acetate layers were washed with water and a saturated aqueous solution of sodium chloride, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (0-30% ethyl acetate in heptane) to obtain 4-oxo-3-propionyl-hexanoic acid ethyl ester (19 g, 68%) as yellow oil.

Provenance & Evidence