[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[CH3:11][C:12]1[CH:17]=[C:16]([C:18]([CH3:20])=[O:19])[CH:15]=[CH:14][CH:13]=1>C(O)(=O)C>[CH2:8]([O:7][C:3](=[O:10])[CH2:20][C:18](=[O:19])[C:16]1[CH:17]=[C:12]([CH3:11])[CH:13]=[CH:14][CH:15]=1)[CH3:9]Sodium hydride (3.1 g, 77.1 mmol) and diethyl carbonate were combined with 3-methylacetophenone (4.5 g, 33.54 mmol). The mixture was stirred for 2 hours at 80° C. After the reaction was completed, ice water and acetic acid were added thereto. Then, the mixture was extracted with ethyl acetate/saturated sodium chloride. The extract was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 3-oxo-3-m-tolylpropionate ethyl ester (5.8 g, yield 84%).
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