[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[OH-].[K+].C1OCCOCCOCCOCCOCCOC1.[CH2:32]([O:34][CH:35]([O:42][CH2:43][CH3:44])[C:36]#[C:37][C:38]([O:40][CH3:41])=[O:39])[CH3:33]>C1COCC1.O>[CH2:43]([O:42][CH:35]([O:34][CH2:32][CH3:33])/[C:36](/[O:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=1)=[CH:37]/[C:38]([O:40][CH3:41])=[O:39])[CH3:44]
To a solution of 2.43 g (15 mmol) of 4-trifluoromethylphenol in 40 mL of THF was added 1.12 g (20 mmol) of powdered KOH and 5.28 g (20 mmol) of 18-crown-6. The solution was heated to 50° C. for 15 minutes, whereupon 3.73 g (20 mmol) of methyl 4,4-diethoxy-2-butynoate was added. The mixture was stirred for 30 minutes, then allowed to cool to room temperature. The solution was then poured into water, and extracted 3 times with 40 mL of ethyl acetate. The organic layers were combined, dried (MgSO4) and concentrated. The crude oil was subjected to column chromatography on SiO2. Elution with 20% ethyl acetatehexane yielded 2.31 g (65%) of an oil, used in the next step without further purification.
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