[H-].[Na+].[CH:3]1([C:9](=[O:11])[CH3:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CO[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.Cl>C1COCC1>[CH:3]1([C:9](=[O:11])[CH2:10][C:14]([C:15]2[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=2)=[O:22])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]10.88 g 60% sodiumhydrid was added 1-cyclohexyl-ethanone in 60 mL THF and stirred for 30 min. Then, 3.25 g 4-fluoro-benzoic acid methyl ester and 200 mg 18-Krone-6 was added to the reaction. The reaction was refluxed 2 h and stirred over night at RT. The reaction was added to 100 mL 1N HCl and extracted with diethylether. The organic layer was concentrated and the residue was purified by chromatography on silica gel and 3 g of the desired compound was obtained.
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