CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH:11]([CH:15]([CH2:18][CH:19]=[CH2:20])[CH2:16][OH:17])([CH2:13][CH3:14])[CH3:12].C(N(CC)CC)C.Cl>ClCCl>[CH:11]([CH:15]([CH2:18][CH:19]=[CH2:20])[CH:16]=[O:17])([CH2:13][CH3:14])[CH3:12]Dimethyl sulfoxide (18.20 mL, 256.4 mmol) was added dropwise over 15 minutes to a dichloromethane (280 mL) solution of oxalic acid chloride (16.90 g, 133.1 mmol) cooled to −78° C., and the mixture was then stirred at −78° C. for 25 minutes. Subsequently, a dichloromethane (75 mL) solution of 2-sec-butylpent-4-en-1-ol (12.20 g, 85.8 mmol) was added dropwise thereto over 30 minutes, and the mixture was stirred at −78° C. for 1 hour. Triethylamine (60.80 g, 600.8 mmol) was added dropwise thereto over 5 minutes, and the mixture was then stirred at room temperature for 2 hours. The mixture was neutralized with 2 N hydrochloric acid (310 mL). The organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain a yellow oil substance as a mixture containing the compound of interest. This compound was used in the next reaction without being further purified.
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