22027-50-5

616-38-6

100-06-1

22027-50-5

Step 1. A solution of p-methoxyacetophenone (30 g, 200 mmol, 1.00 eq.) was added to a 500-mL three-necked round-bottom flask. Sodium hydride (13.6 g, 340 mmol, 1.70 equiv, 60% dispersed in mineral oil) was added in batches. The reaction was stirred at 50 °C for 10 minutes. The reaction mixture was slowly poured into 400 mL of ice water and the resulting solution was washed with ether (50 mL x 2) and subsequently acidified with acetic acid. The aqueous phase was extracted with ethyl acetate (200 mL x 3) and the organic phases were combined. The organic phase was dried sequentially with saturated sodium bicarbonate solution and sodium sulfate. The organic phase was concentrated under reduced pressure to give 37 g (87% yield) of methyl 3-(4-methoxyphenyl)-3-oxopropionate as a yellow oil.