C[Si](C)(C)[O:3][C:4](=[CH:6][CH2:7][CH3:8])[CH3:5].[C:11](Cl)(=[O:16])[CH2:12][C:13](Cl)=[O:14]>CCOCC>[CH2:7]([C:6]1[C:11]([OH:16])=[CH:12][C:13](=[O:14])[O:3][C:4]=1[CH3:5])[CH3:8]In 200 mL of ether, was dissolved 13.6 g (85.9 mmol) of 2-trimethylsilyloxy-2-pentene, and 4.6 mL (47.3 mmol) of malonyl chloride was added dropwise to the solution while stirring the solution at −78° C. After the addition of malonyl chloride, the solution was stirred for 1 hour at −78° C., and then, stirred over night while gradually heating the solution to room temperature. The precipitate was filtered and washed with ether. As a result, 3.08 g (20.0 mmol, 42.3%) of 5-ethyl-4-hydroxy-6-methyl-2-pyrone was obtained.
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