Ethyl bromoacetate → Ethyl 3-acetyl-4-oxopentanoate

Participants

Reaction Steps

A solution of 28.2 ml (0.275 moles) of 2,4-pentanedione and 27.7 ml (0.25 moles) of ethyl bromoacetate in 50 ml of acetone was stirred under nitrogen while 38.0 g (0.275 moles) of dry potassium carbonate, predried at 100° C. under vacuum for 18 hours, was added. The mixture was heated to reflux for 4.5 hours. After cooling, the mixture was separated by filtration and the solid was washed with two portions of 50 ml of acetone. The filtrate was concentrated to dryness, dissolved in methylene chloride, filtered through Fluorosil, concentrated under vacuum to dryness, leaving a residual oil which was distilled. The fraction distilling at 48°-52° C. at 0.05 mm pressure was collected and 26.5 g of ethyl 3-acetyl-4-oxopentanoate were obtained.

Provenance & Evidence