[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([CH2:15][F:16])([C:13]#[CH:14])[CH2:11][F:12])=[CH:5][CH:4]=1.CCCCCC.C([Li])CCC.Cl[C:31]([O:33][CH3:34])=[O:32]>C(OCC)C>[F:16][CH2:15][C:10]([CH2:11][F:12])([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:18])[F:1])=[CH:4][CH:5]=1)[C:13]#[C:14][C:31]([O:33][CH3:34])=[O:32]An amount (0.53 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-yl 4-trifluoromethylphenyl ether was dissolved in diethyl ether (3 ml); to the solution under cooling with ice, a hexane solution (1.4 ml) of 1.69 M n-butyllithium was added dropwise under a nitrogen atmosphere. After the end of the dropwise addition, the mixture was stirred for 1 hour under cooling with ice. The resulting mixture was added dropwise to a solution of methyl chloroformate (0.38 g) in diethyl ether (3 ml) under a nitrogen atmosphere under cooling with ice. After stirring the mixture for 1 hour under cooling with ice, hexane was added, followed by washing with water and a saturated aqueous solution of sodium chloride. The mixture was dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluent; hexane/methylene chloride=1/1) to give the titled compound (0.51 g).
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