[CH2:1]([O:5][C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[C:11]([F:19])[CH:12]=[CH:13][CH:14]=3)[CH2:9][C:8]=2[C:7]=1[F:20])[CH2:2][CH2:3][CH3:4].C([Li])CCC.CC(C)([O-])C.[K+].[CH:32](=[O:35])[CH2:33][CH3:34].Cl>O>[CH2:1]([O:5][C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[C:11]([F:19])[C:12]([CH:32]([OH:35])[CH2:33][CH3:34])=[CH:13][CH:14]=3)[CH2:9][C:8]=2[C:7]=1[F:20])[CH2:2][CH2:3][CH3:4]The metallation of 23 mmol of 2-butoxy-1,8-difluorofluorene with 25 mmol of n-butyllithium (1.6 M solution in hexane) and 25 mmol of potassium tert-butoxide is effected in a similar manner to the procedure described in Example 1. 28 mmol mmol of propionaldehyde are subsequently added dropwise at ≦−70° C. and the mixture is allowed to thaw gradually. The reaction mixture is admixed at −10° C. with 50 ml of water and acidified to pH I using concentrated hydrochloric acid. The mixture is extracted using tert-butyl methyl ether, the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate, and the solvent is removed under reduced pressure. Chromatography on silica gel using dichloromethane as eluent provides 2-butoxy-1,8-difluoro-7-(1-hydroxypropyl)fluorene.
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