[Cl-].[Cl-].[CH2:3]([Al+2])[CH3:4].[CH2:6](Cl)Cl.[CH2:9]([C:13]([OH:25])([CH2:21][CH2:22][CH2:23][CH3:24])[C@@H](OS(C)(=O)=O)C)[CH2:10][CH2:11]C>P(=O)(O)(O)O.C(OCC)(=O)C>[CH3:6][C@@H:9]([CH2:10][CH2:11][CH2:3][CH3:4])[C:13](=[O:25])[CH2:21][CH2:22][CH2:23][CH3:24]After 0.95 ml (0.95 mmol) of ethylaluminum dichloride (hexane 1M solution) were added to a dried methylene chloride (3 ml) solution of 101.5 mg (0.38 mmol) of (S)-3-butyl-2-methanesulfonyloxy-3-heptanol (unrefined) at -78° C. under stirring, and stirred for two and a half hours at -78° C., the temperature was raised to 0° C. over an hour and a half. The reaction was stopped with three drops of phosphoric acid buffer solution (pH 7). The resultant suspension was diluted with ethyl acetate, dried with anhydrous sodium sulfate, filtered and concentrated. The oily residue was separated and refined by the use of silica gel column chromatography (hexane/ethyl acetate=35/1) to obtain (S)-6-methyl-5-decanone as a pale yellow oily substance (56.3 mg, yield 87%).
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